2-(3,5-Difluorophenyl)ethan-1-amine → (4-{3-[(Azetidin-3-yl-ethyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3,5-difluoro-phenyl)-ethyl]-amine

HRID 14899Notes

Reaction equation

HRID 14899 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])C1)=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>>[NH:8]1[CH2:13][CH:12]([N:11]([CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:40][CH2:39][CH2:38][C:33]4[CH:34]=[C:35]([F:37])[CH:36]=[C:31]([F:30])[CH:32]=4)[N:23]=3)[CH:19]=[CH:20][CH:21]=2)[CH2:10][CH3:29])[CH2:14]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 58603699(4-{3-[(Azetidin-3-yl-ethyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3,5-difluoro-phenyl)-ethyl]-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 425. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.74 (s, 1H), 8.38 (d, 2H), 7.97 (d, 1H), 7.71 (m, 2H), 7.90 (d, 2H), 6.74 (s, 1H), 4.58 (m, 5H), 4.07 (m, 4H), 3.25 (q, 2H), 3.07 (t, 2H), 1.39 (t, 3H).

Sources & evidence

ORD record
ord-bb2e48b8603c40cb9f7d224acc783ad7
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

Loading…