2-(3-Fluorophenyl)ethanamine → {4-[3-(2,2-Dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-[2-(3-fluoro-phenyl)-ethyl]-amine

HRID 14949Notes

Reaction equation

HRID 14949 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[C:10]([CH3:29])([CH3:28])[CH2:9]1)=O)(C)(C)C.[F:30][C:31]1[CH:32]=[C:33]([CH2:37][CH2:38][NH2:39])[CH:34]=[CH:35][CH:36]=1>>[CH3:29][C:10]1([CH3:28])[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:39][CH2:38][CH2:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([F:30])[CH:32]=3)[N:22]=2)[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 866033244-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59341046{4-[3-(2,2-Dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-[2-(3-fluoro-phenyl)-ethyl]-amine

Procedure

Intermediate 141 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+H3O+of 438. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.75 (s, 1H) 8.36 (d, 2H) 7.96 (d, 1H) 7.65 (m, 2H) 7.27 (m, 1H) 7.18 (m, 2H)) 6.92 (m, 1H) 4.54 (s, 2H) 3.96 (t, 2H) 3.72 (s, 2H) 3.59 (t, 2H) 3.35 (t, 2H) 3.08 (t, 2H) 1.74 (s, 6H).

Sources & evidence

ORD record
ord-18d08b03d4f24bd592a99fe52f69530f
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

Loading…