2-(2-Chlorophenyl)ethylamine → N-(3-Amino-propyl)-N-(3-{2-[2-(2-chloro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

HRID 14727Notes

Reaction equation

HRID 14727 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:14])=[O:13])(C)(C)C.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][CH2:39][NH2:40]>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:40][CH2:39][CH2:38][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[Cl:31])[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:13])=[O:14]

Participants

3

Reactant 2

HCID 831172-(2-Chlorophenyl)ethylamineHCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 58603541N-(3-Amino-propyl)-N-(3-{2-[2-(2-chloro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Procedure

Intermediate 4 was coupled to 2-(2-chloro-phenyl)-ethylamine following procedure F and the resulting product deprotected by procedure G. LC-MS showed the product had the expected M+H+ of 474. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.8 (m, 1H) 8.18 (m, 4H) 7.6 (m, 6H) 4.45 (s, 2H) 3.95 (m, 2H) 3.4 (m, 2H) 3.18 (m, 4H) 3.0 (m, 2H) 2.9 (s, 3H) 1.75 (m, 2H).

Sources & evidence

ORD record
ord-317d244a6ef14275b1e062ab62fd2123
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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