.4, 128.four, 127.4, 118.9, 105.two, 67.06, 45.three, 36.9, 12.5; HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C22H25N
.4, 128.four, 127.4, 118.9, 105.2, 67.06, 45.3, 36.9, 12.five; HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C22H25N2O2 349.1911, Discovered 349.1898. (9H-Fluoren-9-yl)methyl (4-(2-(2,5-dimethyl-1H-pyrrol-1yl)ethyl)phenyl)carbamate (14c)–Yield 421 mg (79 ); pale white solid; mp 227 – 229 ; Rf = 0.2 (EtOAc/hexanes, 1:7-1:four); 1H NMR (500 MHz, CDCl3) 7.86 – 7.71 (m, 2H), 7.68 – 7.56 (m, 2H), 7.49 – 7.36 (m, 2H), 7.40 – 7.29 (m, 4H), 7.01 (d, J = 7.9 Hz, 2H), six.62 (s, 1H), five.76 (s, 2H), four.54 (d, J = six.6 Hz, 2H), four.44 (d, J = 6.six Hz, 1H), 3.91 (t, J = 7.6 Hz, 2H), 2.84 (t, J = 7.6 Hz, 2H), 2.13 (s, 6H); 13C NMR (126 MHz, CDCl3) 155.eight, 143.7, 141.four, 129.five, 127.eight, 127.six, 127.4, 127.1, 127.0, 124.9, 120.1, 119.9, 105.2, 66.9, 47.1, 45.3, 36.eight, 12.four; HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C29H29N2O2 437.2224, Located 437.2224. 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-5-nitropyridine (19)–Yield 145 mg (82 ); yellow crystals; mp 206 – 208 ; Rf = 0.4 (EtOAc/hexanes, 1:19-1:9); 1H NMR (500 MHz, CDCl3) 9.45 (s, 1H), eight.63 (d, J = eight.eight Hz, 1H), 7.40 (d, J = eight.7 Hz, 1H), 6.00 (s, 2H), 2.25 (s, 6H); 13C NMR (126 MHz, CDCl3) 156.1, 145.1, 142.1, 133.2, 129.1, 120.7, 109.three, 13.eight; LRMS (ESI): m/z = 218.09 [M + H]+. The information had been in IDO Compound accordance with these previously reported.26 5-Chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)benzonitrile (21)–Yield 66.9 mg (78 ); yellow crystals; mp = 106 – 108 ; Rf = 0.3 (EtOAc/hexanes, 1:19-1:9); 1H NMR (500 MHz, CDCl3) 7.77 (d, J = 2.four Hz, 1H), 7.68 (dd, J = 8.5, 2.four Hz, 1H), 7.30 (d, J = eight.5 Hz, 1H), five.97 (s, 2H), 2.02 (s, 6H); 13C NMR (126 MHz, CDCl3) 140.6, 134.six, 134.0, 133.1, 131.three, 128.8, 114.9, 114.7, 107.five, 12.eight; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C13H11ClN2Na 253.0503, Discovered 253.0506. Compounds 13a-c have been synthesized by a process described in V. Perron et al.20 for selective protection of an aromatic amine. tert-Butyl (4-(2-aminoethyl)phenyl)carbamate (13a)–Yield 405 mg (78 ); white strong; mp = 88 – 91 ; 1H NMR (500 MHz, MeOD) 7.38 (d, J = eight.0 Hz, 2H), 7.11 (d, J = 8.4 Hz, 2H), two.84 (t, J = 7.2 Hz, 2H), 2.69 (t, J = 7.two Hz, 2H), 1.52 (s, 9H); 13C NMR (126 MHz, MeOD) 155.4, 138.9, 134.9, 130.two, 120.1, 80.7, 44.1, 39.0, 28.9; LRMS (ESI): m/z = 259.15 [M + Na]+. The data had been in accordance with these previously reported.NIH-PA Author ALK1 MedChemExpress Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptBenzyl (4-(2-aminoethyl)phenyl)carbamate (13b)–Yield 438 mg (81 ); pale yellow strong; mp 151 – 153 ; 1H NMR (500 MHz, CD3OD): = 7.30.42 (m, 7H), 7.13 (d, J=8.six Hz, 2H), 5.16 (s, 2H), two.87 (t, J=6.eight Hz, 2H), 2.72 (t, J = 7.0 Hz, 2H); 13C NMR (126 MHz, CD3OD): 155.9, 142.7, 138.five, 138.2, 135.4, 130.2, 129.6, 129.4, 129.1, 129.0, 128.three, 128.0, 120.2, 67.5, 65.3, 44.1, 39.1; LRMS (ESI): m/z = 271.14 [M + H]+. The data had been in accordance with these previously reported.19 (9H-Fluoren-9-yl)methyl (4-(2-aminoethyl)phenyl)carbamate (13c)–Yield 472 mg (79 ); white solid; mp 207 – 209 ; H NMR (500 MHz, DMSO-d6): 7.92.05 (m, 2H), 7.89 (d, J = 7.six Hz, 2H), 7.73 (d, J = 7.4 Hz, 2H), 7.31.43 (m, 4H), 7.13 (d, J = 8.2 Hz, 2H), 4.45 (d, J = six.7 Hz, 2H), four.28 (t, J = six.five Hz, 1H), two.93.97 (m, 2H), two.78.82 (m, 2H); 13C NMR (126 MHz, DMSO-d6): 153.47, 143.66, 140.73, 137.54, 131.25, 128.97,J Org Chem. Author manuscript; offered in PMC 2014 November 01.Walia et al.Page127.72, 127.13, 125.09, 120.14, 118.57, 66.28, 46.54, 32.19, 21.03; LRMS (ESI): m/z = 359.17 [M + H]+. The information were in accordance with those previously reported.NIH-PA Author Manuscript NIH.
