2-(3,5-Difluorophenyl)ethan-1-amine → 1-(3-{2-[2-(3,5-Difluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-piperazine-2-carboxylic acid

HRID 14943Notes

Reaction equation

HRID 14943 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[C:18]([OH:20])=[O:19])[CH:5]=[CH:4][N:3]=1.[F:24][C:25]1[CH:26]=[C:27]([CH2:32][CH2:33][NH2:34])[CH:28]=[C:29]([F:31])[CH:30]=1>>[F:24][C:25]1[CH:26]=[C:27]([CH2:32][CH2:33][NH:34][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=3)[CH2:11][N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH:13]3[C:18]([OH:20])=[O:19])[CH:5]=[CH:4][N:3]=2)[CH:28]=[C:29]([F:31])[CH:30]=1

Participants

3

Reactant 2

HCID 36736652-(3,5-Difluorophenyl)ethan-1-amineHCID 866033201-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-piperazine-2-carboxylic acid

Product 1

HCID 586035911-(3-{2-[2-(3,5-Difluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-piperazine-2-carboxylic acid

Procedure

Intermediate 137 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 454. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.47 (s, 1H) 8.36 (d, 1H)) 8.33 (d, 1H) 7.87 (d, 1H) 7.71 (t, 1H) 7.65 (d, 1H) 7.00 (d, 2H) 6.77 (s, 1H) 4.63 (dd, 1H) 4.36 (s, 2H) 4.08 (t, 2H) 3.84 (dd, 2H) 3.65 (t, 2H) 3.47 (t, 2H) 3.09 (t, 2H).

Sources & evidence

ORD record
ord-d9bac519694943318bd424dd3dc84b70
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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