2-(3,5-Difluorophenyl)ethan-1-amine → [2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(S),6(R)-dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

HRID 14898Notes

Reaction equation

HRID 14898 reaction equation
C(OC([N:8]1[CH2:13][CH:12]([CH3:14])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:17]=2)[CH:10]([CH3:29])[CH2:9]1)=O)(C)(C)C.[F:30][C:31]1[CH:32]=[C:33]([CH2:38][CH2:39][NH2:40])[CH:34]=[C:35]([F:37])[CH:36]=1>>[F:30][C:31]1[CH:32]=[C:33]([CH2:38][CH2:39][NH:40][C:24]2[N:23]=[C:22]([C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][N:11]4[C@H:10]([CH3:29])[CH2:9][NH:8][CH2:13][C@@H:12]4[CH3:14])[CH:17]=3)[CH:27]=[CH:26][N:25]=2)[CH:34]=[C:35]([F:37])[CH:36]=1

Participants

3

Reactant 2

HCID 36736652-(3,5-Difluorophenyl)ethan-1-amineHCID 866033084-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603503[2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(S),6(R)-dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

Procedure

Intermediate 114 was coupled with 2-(3,5-difluoro-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 439. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.57 (s, 1H), 8.36 (t, 2H), 7.94 (d, 1H), 7.74 (m, 2H), 6.99 (d, 2H), 6.75 (t, 1H), 3.77 (m, 5H), 3.64 (m, 5H), 3.07 (t, 2H), 1.69 (d, 6H).

Sources & evidence

ORD record
ord-f0c89bfb5a774034a67c2022beb836ce
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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