2-(3-Fluorophenyl)ethanamine → {4-[3-(2-Ethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-[2-(3-fluoro-phenyl)-ethyl]-amine
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]([CH2:28][CH3:29])[CH2:9]1)=O)(C)(C)C.[F:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[CH2:34][CH2:35][NH2:36]>>[CH2:28]([CH:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:36][CH2:35][CH2:34][C:33]3[CH:37]=[CH:38][CH:39]=[C:31]([F:30])[CH:32]=3)[N:22]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:29]Participants
3
Procedure
Intermediate 130 was coupled with 3-fluorophenethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 420. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.25-8.4 (m, 2H) 7.8 (d, 1H) 7.7 (t, 1H) 7.5 (d, 1H) 7.18-7.35 (m, 2H) 7.05-7.15 (m, 2H) 6.9 (m, 1H) 4.72 (d, 1H) 4.1 (d, 1H) 3.92 (br s, 2H) 3.65 (m, 1H) 3.3-3.5 (m, 6H) 3.12 (m, 1H) 3.05 (m, 2H) 2.18 (m, 1H) 1.92 (m, 1H) 1.1 (t, 3H).
Sources & evidence
- ORD record
- ord-88c780f17c86461f9f4795e9bbc972cc
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732444B2
Reaction notes
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