Methylamine → 6-Oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid methylamide
Reaction equation
CO[C:3]([C:5]1[NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:17](=[O:18])[NH:16][CH2:15][CH2:14][C:13]=1[C:12]=23)=[O:4].[CH3:19][NH2:20]>CO>[CH3:19][NH:20][C:3]([C:5]1[NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:17](=[O:18])[NH:16][CH2:15][CH2:14][C:13]=1[C:12]=23)=[O:4]Participants
Procedure
6-Oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid methyl ester (50 mg, 0.20 mmol) was suspended in 1 mL of a 33% solution of methylamine in methanol. The suspension was stirred at room temperature for 21 h. Another 2 mL 33% methylamine in methanol was added and the resulting solution stirred another 8 h at room temperature then 15 h at 30° C. The reaction mixture was concentrated in vacuo leaving a yellow solid which was crystallized from DMF/MeOH/CHCl3 to yield 6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid methylamide, 36 mg (72%) as a yellow solid: m.p. 321-322° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 2.81 (s, 3H), 3.15 (m, 2H), 3.40 (m, 2H), 7.32 (app t, J=7.8 Hz, 1H), 7.61 (d, J=8.1Hz, 1H), 7.74 (d, J=7.5 Hz, 1H), 7.95 (br q, 1H), 8.09 (br t, 1H), 11.46 (br s, 1H). MS (electrospray, [M+Na]+) 266. Anal. (C13H13N3O2.0.4 H2O) C, H, N.
Workup
- stirringthe resulting solution stirred another 8 h at room temperature
- custom15 h
- customat 30° C
- concentrationThe reaction mixture was concentrated in vacuo
- customleaving a yellow solid which
- customwas crystallized from DMF/MeOH/CHCl3
Sources & evidence
- ORD record
- ord-b0be6afd6f0a449c85ae53b2ce38ce51
- Source dataset
- uspto-grants-2005_12
- Patent number
- US06977298B2
Reaction notes
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