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

HRID 14950Notes

Reaction equation

HRID 14950 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]([CH2:38][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: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:10]4([CH3:29])[CH3:28])[CH:16]=3)[CH:26]=[CH:25][N:24]=2)[CH:34]=[C:35]([F:37])[CH:36]=1

Participants

3

Reactant 2

HCID 36736652-(3,5-Difluorophenyl)ethan-1-amineHCID 866033244-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603667[2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2,2-dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

Procedure

Intermediate 141 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+H3O+of 456. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.76 (s, 1H) 8.36 (d, 1H) 8.33 (d, 1H) 7.97 (d, 1H) 7.70 (t, 2H) 7.03 (d, 2H) 6.76 (m, 1H) 4.54 (s, 2H) 3.98 (t, 2H) 3.72 (s, 2H) 3.35 (m, 4H) 3.10 (t, 2H) 1.74 (s, 6H).

Sources & evidence

ORD record
ord-2d0e6ee7e03d4cf2b68f06db08723afc
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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