Methanesulfonyl chloride → N-(3-{2-[2-(3-Chloro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-ethyl-methanesulfonamide

HRID 14802Notes

Reaction equation

C(OC(N1CC[CH:10]([N:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH2:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=4)[N:26]=3)[CH:20]=2)[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:9]1)=O)(C)(C)C.CS([Cl:45])(=O)=O>>[Cl:45][C:36]1[CH:35]=[C:34]([CH2:33][CH2:32][NH:31][C:27]2[N:26]=[C:25]([C:21]3[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=3)[CH2:18][N:13]([CH2:10][CH3:9])[S:14]([CH3:17])(=[O:16])=[O:15])[CH:30]=[CH:29][N:28]=2)[CH:39]=[CH:38][C:37]=1[OH:40]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 670448323-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603440N-(3-{2-[2-(3-Chloro-4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-ethyl-methanesulfonamide

Procedure

Compound 94 was coupled with methanesulfonyl chloride following procedure D. LC-MS showed the product had the expected M+H+ of 461. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.3 (d, 1H) 8.1 (s, 1H) 8.0 (s, 1H) 7.5 (d, 2H) 7.3 (m, 1H) 7.2 (s, 1H) 7.1 (d, 1H) 7.0 (d, 1H) 6.9 (d, 1H) 4.4 (s, 2H) 3.5 (m, 2H) 3.2 (m, 2H) 3.0 (s, 3H) 2.8 (m, 2H) 1.0 (m, 3H).

Sources & evidence

ORD record: ord-e4b93980c2544ee6aed9376ea16866d6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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