Cyclopentylamine → 6-Chloro-N-cyclopentyl-2-{4-[2-(4-morpholinyl)ethoxy]phenyl}-1H-imidazo[4,5-b]pyridin-7-amine
Reaction equation
[Cl:1][C:2]1[C:3](Cl)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH:27]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28]1>>[Cl:1][C:2]1[C:3]([NH:32][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:4]2[NH:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:15][CH:16]=3)=[N:8][C:5]2=[N:6][CH:7]=1Participants
3
Procedure
6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (30 mg, 7.6 μmol) and cyclopentylamine (1 ml) were heated in a microwave oven (170-° C.: 30 min). The excess amine was removed in vacuo and the residue dissolved in acetonitrile (1 ml) with a drop of TFA. This mixture was subjected to semi-preparative HPLC-C18. The appropriate fractions were pooled and evaporated in vacuo. The residue was dissolved in EtOAc (5 ml). This solution was washed with saturated aqueous NaHCO3 (5 ml) and brine (2 ml). The organic phase was dried (MgSO4) and evaporated in vacuo and the residue recrystallized from methanol to afford the pure product (16 mg, 47%).
Workup
- customThe excess amine was removed in vacuo
- dissolutionthe residue dissolved in acetonitrile (1 ml) with a drop of TFA
- customevaporated in vacuo
- dissolutionThe residue was dissolved in EtOAc (5 ml)
- washThis solution was washed with saturated aqueous NaHCO3 (5 ml) and brine (2 ml)
- dry with materialThe organic phase was dried (MgSO4)
- customevaporated in vacuo
- customthe residue recrystallized from methanol
Sources & evidence
- ORD record
- ord-53453a12e4134402a576efe541b78771
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07410966B2
Reaction notes
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