Benzoic Acid → N-{3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-benzamide

HRID 14747

Reaction equation

HRID 14747 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](O)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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][C:33](=[O:40])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:22]=[CH:21][N:20]=2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 243Benzoic AcidHCID 59341031N-(3-Amino-propyl)-N-(3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Product 1

HCID 58603490N-{3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-propyl}-benzamide

Procedure

Compound 2 was coupled with benzoic acid by procedure K. LC-MS showed the product had the expected M+H+ of 560. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.35 ppm) 8.5 (d, 1H) 8.2 (d, 1H) 8.1 (s, 1H) 8.0 (d, 2H) 7.6 (d, 2H), 7.4 (m, 5H), 7.1 (m, 2H), 6.7 (d, 2H), 4.4 (s, 2H), 3.6 (t, 2H), 3.23 (d, 2H), 2.9 (s, 3H), 2.8 (t, 2H), 1.8 (m, 2H).

Sources & evidence

ORD record
ord-df4854ccb6084b47aa659485b466ef78
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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