2-(3-Fluorophenyl)ethanamine → [2-(3-Fluoro-phenyl)-ethyl]-{4-[3-(2-piperidin-4-yl-ethyl)-phenyl]-pyrimidin-2-yl}-amine

HRID 14896

Reaction equation

HRID 14896 reaction equation
C(N([CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29](O)=[C:28]([F:33])[CH:27]=3)[N:18]=2)[CH:14]=[CH:15][CH:16]=1)C1CCNCC1)C.FC1[CH:36]=[C:37]([CH2:41][CH2:42][NH2:43])[CH:38]=[CH:39]C=1>>[F:33][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][NH:23][C:19]2[N:18]=[C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:36][CH:37]4[CH2:41][CH2:42][NH:43][CH2:39][CH2:38]4)[CH:12]=3)[CH:22]=[CH:21][N:20]=2)[CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 670456434-[2-(4-{3-[(Ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-2-fluoro-phenol

Product 1

HCID 58603492[2-(3-Fluoro-phenyl)-ethyl]-{4-[3-(2-piperidin-4-yl-ethyl)-phenyl]-pyrimidin-2-yl}-amine

Procedure

Intermediate 92 was coupled with 2-(3-fluoro-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 406. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.27 (d, 1H), 8.04 (s, 1H), 7.96 (m, 1H), 7.47 (d, 2H), 7.25 (m, 2H), 7.09 (d, 1H), 7.04 (d, 1H), 6.89 (t, 1H), 3.80 (m, 2H), 3.36 (m, 2H), 2.91 (m, 4H), 2.77 (t, 2H), 2.00 (d, 2H), 1.67 (m, 3H), 1.36 (m, 2H).

Sources & evidence

ORD record
ord-b8dfdda9b16146e69683b1f068aa6cfb
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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