3-Chlorophenethylamine → N-(3-{2-[2-(3-Chloro-phenyl)-ethylamino]-5-fluoro-pyrimidin-4-yl}-benzyl)-N-piperidin-4-yl-methanesulfonamide

HRID 14852Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[C:31]([F:32])=[CH:30][N:29]=[C:28](Cl)[N:27]=3)[CH:21]=2)[S:15]([CH3:18])(=[O:17])=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:34][C:35]1[CH:36]=[C:37]([CH2:41][CH2:42][NH2:43])[CH:38]=[CH:39][CH:40]=1>>[Cl:34][C:35]1[CH:36]=[C:37]([CH2:41][CH2:42][NH:43][C:28]2[N:27]=[C:26]([C:22]3[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=3)[CH2:19][N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[S:15]([CH3:18])(=[O:17])=[O:16])[C:31]([F:32])=[CH:30][N:29]=2)[CH:38]=[CH:39][CH:40]=1

Participants

Reactant 2

HCID 1393813-Chlorophenethylamine

HCID 866032884-{[3-(2-Chloro-5-fluoro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603443N-(3-{2-[2-(3-Chloro-phenyl)-ethylamino]-5-fluoro-pyrimidin-4-yl}-benzyl)-N-piperidin-4-yl-methanesulfonamide

Procedure

Intermediate 77 was coupled with 2-(3-chloro-phenyl)-ethylamine following procedure Q. The resulting product was deprotected following procedure R. LC-MS showed the product had the expected M+H+ of 518. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.25 (d, 1H), 8.18 (s, 1H), 7.97 (d, 1H), 7.49 (m, 2H), 7.15 (m, 4H), 4.56 (s, 2H), 3.93 (m, 1H), 3.64 (t, 2H), 3.33 (m, 2H), 3.04 (s, 3H), 2.98 (m, 2H), 2.91 (t, 2H), 1.91 (m, 4H).

Sources & evidence

ORD record: ord-cd09b57ed6074f969aaf7a6bd2fac7e6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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