Phenylmethanesulfonyl chloride → N-{3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-C-phenyl-methanesulfonamide

HRID 14754

Reaction equation

HRID 14754 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[N:18]=2)[CH:12]=1)[S:6]([CH3:9])(=[O:8])=[O:7].[C:33]1([CH2:39][S:40](Cl)(=[O:42])=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[OH:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][NH:23][C:19]2[N:18]=[C:17]([C:13]3[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=3)[CH2:10][N:5]([S:6]([CH3:9])(=[O:8])=[O:7])[CH2:4][CH2:3][CH2:2][NH:1][S:40]([CH2:39][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:42])=[O:41])[CH:22]=[CH:21][N:20]=2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 59341031N-(3-Amino-propyl)-N-(3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Product 1

HCID 58603706N-{3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-C-phenyl-methanesulfonamide

Procedure

Compound 2 was coupled with phenyl-methanesulfonyl chloride following procedure D. LC-MS showed the product had the expected M+H+ of 610. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.3 (d, 1H), 8.0 (d, 1H) 7.5 (m, 3H) 7.3 (d, 2H), 7.2 (m, 4H), 6.7 (d, 4H), 4.4 (s, 2H), 4.2 (s, 2H), 3.6 (t, 2H), 3.2 (t, 2H), δ 2.9 (s, 3H), 2.7 (t, 2H), 2.7 (t, 2H), δ 1.6 (m, 2H).

Sources & evidence

ORD record
ord-b4af718ec3cb462699228b170e79463f
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

Loading…