2-(6-fluoro-1H-indol-3-yl)ethanamine → N-(3-Amino-propyl)-N-(3-{2-[2-(6-fluoro-1H-indol-3-yl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

HRID 14718Notes

Reaction equation

HRID 14718 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.[F:31][C:32]1[CH:40]=[C:39]2[C:35]([C:36]([CH2:41][CH2:42][NH2:43])=[CH:37][NH:38]2)=[CH:34][CH:33]=1>>[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:43][CH2:42][CH2:41][C:36]3[C:35]4[C:39](=[CH:40][C:32]([F:31])=[CH:33][CH:34]=4)[NH:38][CH:37]=3)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:13])=[O:14]

Participants

3

Reactant 2

HCID 8540242-(6-fluoro-1H-indol-3-yl)ethanamineHCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 58603389N-(3-Amino-propyl)-N-(3-{2-[2-(6-fluoro-1H-indol-3-yl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Procedure

Intermediate 4 was coupled with 2-(6-Fluoro-1H-indol-3-yl)-ethylamine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 497. 1H NMR (Varian 300 MHz, CDCl3—CD3OD, shifts relative to the solvent peak at 7.24 ppm) δ 8.1 (m, 2H) 7.8 (d, 1H) 7.5 (m, 4H) 7.3 (m, 1H) 6.8 (m, 2H) 4.4 (d, 2H) 3.9 (m, 1H) 3.6 (m, 2H) 3.3 (m, 2H) 3.1 (m, 1H) 2.8 (m, 5H) 1.7 (m, 2H).

Sources & evidence

ORD record
ord-755f76244b554581a2c45f93b97a61d8
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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