Phenol → 4-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2-(R)-methyl-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
C1(O)C=CC=CC=1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([Cl:34])[N:29]=3)[CH:23]=2)[CH2:17][C@@H:16]1[CH3:35])=[O:14])([CH3:11])([CH3:10])[CH3:9].NCCC1C=CC(O)=CC=1>>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([Cl:34])[N:29]=3)[CH:23]=2)[CH2:17][C@H:16]1[CH3:35])=[O:14])([CH3:11])([CH3:9])[CH3:10]Participants
4
Procedure
442-{4-[3-(3-S-Methyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol: Intermediate 128 4-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2-(S)-methyl-piperazine-1-carboxylic acid tert-butyl ester was coupled with tyramine following procedure F then deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 404. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.6 (s, 1H) 8.4 (m, 2H) 7.9 (s, 1H) 7.6 (d, 2H) 7.1 (s, 2H) 6.7 (a, 2H) 4.6 (S, 2H) 3.9 (s, 2H) 3.6 (m, 7H) 2.9 (s, 2H) 1.4 (s, 3H).
Sources & evidence
- ORD record
- ord-80d3f8b249bf4f46bbf1a4c3fda3e742
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268822B2
Reaction notes
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