2-(3-Fluorophenyl)ethanamine → 2-Fluoro-4-[2-(4-{3-[(piperidin-4-yl-propyl-amino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

HRID 14874

Reaction equation

HRID 14874 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]([CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[CH2:25][CH2:26][CH3:27])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:6][CH:7]=1.C([O:38]C(N1CCC(N(CC2C=CC=C(C3C=CN=C(Cl)N=3)C=2)CCC)CC1)=O)(C)(C)C.FC1C=C(C=CC=1)CCN>>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]([CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[CH2:25][CH2:26][CH3:27])[CH:18]=3)[CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[OH:38]

Participants

4

Reactant 3

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 586034612-(3-Fluoro-phenyl)-ethyl-(4-{3-[(piperidin-4-yl-propyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-amineHCID 866032954-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-propyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586036462-Fluoro-4-[2-(4-{3-[(piperidin-4-yl-propyl-amino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

Procedure

[2-(3-Fluoro-phenyl)-ethyl-(4-{3-[(piperidin-4-yl-propyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-amine: Intermediate 93 was coupled with 3-fluorophenethylamine following procedure F. The resulting product was deprotected following procedure G. The product was purified by HPLC. LC-MS showed the product had the expected M+H+ of 448. 1H NMR (Varian 300 MHz, DMSO, shifts relative to the solvent peak at 2.50 ppm) δ 8.3 (d, 1H), 8.0 (s, 1H), 7.9 (d, 1H), 7.4 (m, 2H), 7.3 (m, 2H), 7.1 (d, 2H), 7.0 (d, 1H), 3.6 (s, 2H), 3.5 (d, 2H), 3.2 (d, 2H), 2.9 (m, 4H), 2.8 (m, 1H), 2.5 (d, 2H), 1.8 (m, 4H), 1.3 (m, 2H), 0.96 (t, 3H).

Workup

  1. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-b689748fd5c6449b902eebbf78d67c9f
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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