Ammonia → HCID 86693511, compound
Reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:30]3[CH2:31][CH:28]([CH2:29]3)[C:8]3[N:9]([CH2:17][C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]([CH3:27])[N:19]=4)[C:10]([C:12]([O:14]CC)=O)=[N:11][C:7]=3[C:6]=2[CH:32]=1.[NH3:33]>>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:30]3[CH2:31][CH:28]([CH2:29]3)[C:8]3[N:9]([CH2:17][C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]([CH3:27])[N:19]=4)[C:10]([C:12]([NH2:33])=[O:14])=[N:11][C:7]=3[C:6]=2[CH:32]=1Participants
3
Conditions
- Temperature
- 50 °C
Procedure
A pressure tube containing a solution of ethyl 9-iodo-3((1-methyl-1H-indazol-3-yl)methyl)-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate (198 mg, 0.37 mmol) in methanolic ammonia (7 mL of 7.0M ammonia in methanol) was warmed to 50° C. for 8 days. After evaporation of the reaction mixture in vacuo, the residue was suspended in methanol (0.8 mL) and the solid collected by vacuum filtration to furnish the title compound as an off-white solid (164 mg, 0.32 mmol, 86%): 1H NMR (250 MHz, CDCl3) δ1.48-1.57 (m, 2H), 2.71-2.87 (m, 2H), 3.52 (td, J=8.15, 4.42 Hz, 1H), 3.79 (td, J=7.54, 3.81 Hz, 1H), 3.99 (s, 3H), 5.44 (br. s., 3H), 6.24 (s, 2H), 6.78 (d, J=7.92 Hz, 1H), 7.03-7.11 (m, 1H), 7.31-7.41 (m, 3H), 7.53 (dt, J=8.22, 0.91 Hz, 1H), 8.71 (d, J=1.83 Hz, 1H); M+H=510.