2-(3-Fluorophenyl)ethanamine → N1-Ethyl-N1-(3-{5-fluoro-2-[2-(3-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-propane-1,3-diamine

HRID 14854

Reaction equation

HRID 14854 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:26]([F:27])=[CH:25][N:24]=[C:23](Cl)[N:22]=2)[CH:16]=1)[CH2:12][CH3:13])(C)(C)C.[F:30][C:31]1[CH:32]=[C:33]([CH2:37][CH2:38][NH2:39])[CH:34]=[CH:35][CH:36]=1>>[CH2:12]([N:11]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:39][CH2:38][CH2:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([F:30])[CH:32]=3)[N:22]=2)[CH:16]=1)[CH2:10][CH2:9][CH2:8][NH2:7])[CH3:13]

Participants

3

Reactant 2

HCID 5339282-(3-Fluorophenyl)ethanamineHCID 86603289(3-{[3-(2-Chloro-5-fluoro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 58603454N1-Ethyl-N1-(3-{5-fluoro-2-[2-(3-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-propane-1,3-diamine

Procedure

Intermediate 78 was coupled with 2-(3-fluoro-phenyl)-ethylamine following procedure Q. The resulting product was deprotected following procedure R. LC-MS showed the product had the expected M+H+ of 426. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.29 (d, 1H), 8.19 (s, 2H), 7.66 (m, 2H), 6.97 (m, 4H), 4.49 (s, 2H), 3.64 (t, 2H), 3.24 (m, 4H), 2.97 (t, 2H), 2.92 (t, 2H), 2.07 (m, 2H), 1.36 (t, 3H).

Sources & evidence

ORD record
ord-defd25637f274359ab7499ddbf7187ed
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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