N-[4-(2-aminoethyl)phenyl]acetamide → N-(4-{2-[4-(3-{[(3-Amino-propyl)-methanesulfonyl-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenyl)-acetamide

HRID 14704

Reaction equation

HRID 14704 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.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:43])[CH3:42])=[CH:36][CH:35]=1>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:43])[CH3:42])=[CH:36][CH:35]=3)[N:24]=2)[CH:20]=[CH:21][CH:22]=1)[S:12]([CH3:15])(=[O:13])=[O:14]

Participants

3

Reactant 2

HCID 12383171N-[4-(2-aminoethyl)phenyl]acetamideHCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 58603580N-(4-{2-[4-(3-{[(3-Amino-propyl)-methanesulfonyl-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenyl)-acetamide

Procedure

Intermediate 4 from above was coupled with N-[4-(2-Amino-ethyl)-phenyl]-acetamide by procedure F and the resulting product deprotected by procedure G to give 3. 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) 8.0 (m, 1H) 7.6 (m, 1H) 7.5 (m, 1H) 7.4 (m, 2H) 7.3 (m, 1H) 7.2 (d, 2H) 4.4 (s, 2H) 3.9 (m, 2H) 3.3 (m, 2H) 2.9 (m, 2H) 2.8 (s, 3H) 2.7 (m, 2H) 2.1 (s, 3H) 1.8 (m, 2H).

Workup

  1. customto give 3

Sources & evidence

ORD record
ord-dd40c32f83b44f7b8e6ec914d1dd932d
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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