2-(3-Fluorophenyl)ethanamine → (4-{3-[(Ethyl-piperidin-3(S)-ylmethyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3-fluoro-phenyl)-ethyl]-amine

HRID 14904Notes

Reaction equation

HRID 14904 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=3)[CH:20]=2)[CH2:16][CH3:17])[CH2:9]1)=O)(C)(C)C.[F:32][C:33]1[CH:34]=[C:35]([CH2:39][CH2:40][NH2:41])[CH:36]=[CH:37][CH:38]=1>>[CH2:16]([N:15]([CH2:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:41][CH2:40][CH2:39][C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([F:32])[CH:34]=3)[N:26]=2)[CH:22]=[CH:23][CH:24]=1)[CH2:14][C@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[CH3:17]

Participants

3

Reactant 2

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 866032973-({[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603558(4-{3-[(Ethyl-piperidin-3(S)-ylmethyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3-fluoro-phenyl)-ethyl]-amine

Procedure

Intermediate 95 was coupled with 2-(3-fluoro-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 449. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.71 (s, 1H), 8.36 (t, 2H), 7.96 (d, 1H), 7.70 (m, 2H), 7.30 (s, 1H), 7.12 (d, 2H), 6.91 (s, 1H), 4.60 (s, 2H), 3.99 (s, 2H), 3.06 (m, 6H), 2.84 (m, 2H), 2.65 (t, 1H), 2.34 (m, 2H), 1.87 (m, 4H), 1.45 (t, 3H).

Sources & evidence

ORD record
ord-f396231134fe4fe2bd2a8f386e5f10c9
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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