Diisopropylethylamine → 4-Methoxy-N-[4-methyl-3-(9H-pyrimido[4,5-b]indol-6-yl)phenyl]-3-(trifluoromethyl)-benzamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[CH3:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]1[N:33]=[CH:34][N:35]=[CH:36][C:27]2=1.CCN(C(C)C)C(C)C>O1CCCC1.CO>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([CH3:16])=[C:18]([C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28]3[N:33]=[CH:34][N:35]=[CH:36][C:27]4=3)[CH:19]=2)=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To 4-methoxy-3-(trifluoromethyl)benzoyl chloride (11.0 μL, 0.070 mmol) was added a solution of 4-methyl-3-(9H-pyrimido[4,5-b]indol-6-yl)aniline (17.5 mg, 0.064 mmol) and DIPEA (16 μL, 0.089 mmol) in tetrahydrofuran (THF) (0.4 mL). The reaction was stirred at ambient temperature until LCMS indicated complete reaction, typically 16 hours. The reaction mixture was diluted to a total of 2 mL with THF and MeOH and purified by preparative LCMS to recover the product as a TFA salt (18.6 mg, 49.4%). 1H NMR (300 MHz, DMSO): δ 13.0 (bs, 1H), 10.33 (s, 1H), 9.64 (s, 1H), 9.13 (s, 1H), 8.35 (s, 1H), 8.24 (m, 2H), 7.7-7.8 (m, 3H), 7.63 (dd, 1H), 7.41 (d, 1H), 7.32 (d, 1H), 2.25 (s, 3H). MS (EI) m/z=477 (M+H).
Workup
- customreaction, typically 16 hours
- custompurified by preparative LCMS
- customto recover the product as a TFA salt (18.6 mg, 49.4%)
Sources & evidence
- ORD record
- ord-5e7d016ace6944ffa1125c7e63b73424
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841318B2
Reaction notes
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