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

HRID 14891Notes

Reaction equation

HRID 14891 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)[CH:10]([CH3:28])[CH2:9]1)=O)(C)(C)C.[F:29][C:30]1[CH:31]=[C:32]([CH2:37][CH2:38][NH2:39])[CH:33]=[C:34]([F:36])[CH:35]=1>>[F:29][C:30]1[CH:31]=[C:32]([CH2:37][CH2:38][NH:39][C:23]2[N:22]=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][N:11]4[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]4[CH3:28])[CH:16]=3)[CH:26]=[CH:25][N:24]=2)[CH:33]=[C:34]([F:36])[CH:35]=1

Participants

3

Reactant 2

HCID 36736652-(3,5-Difluorophenyl)ethan-1-amineHCID 866033054-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3-methyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603705[2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(R)-methyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

Procedure

Intermediate 111 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 8.72 (s, 1H), 8.36 (t, 2H), 7.97 (d, 1H), 7.73 (d, 1H), 7.69 (d, 1H), 7.01 (d, 2H), 6.72 (s, 1H), 4.43 (d, 1H), 4.05 (m, 3H), 3.55 (m, 6H), 3.39 (m, 1H), 3.06 (t, 2H), 1.77 (d, 3H).

Sources & evidence

ORD record
ord-5a45ca84402f4cf58dd41ec54ba5efec
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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