HCID 66734063, compound → 8-[2-(2,5-Difluoro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-1-iodo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine
Reaction equation
[CH2:1]([C:3]1[N:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[C:6]([I:8])[N:7]=1)[CH3:2].[F:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[C:16]([F:23])=[CH:15][C:14]=1[CH2:24][CH2:25][CH:26]=O>>[F:12][C:13]1[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[C:16]([F:23])=[CH:15][C:14]=1[CH2:24][CH2:25][CH:26]1[NH:11][CH2:10][CH2:9][N:4]2[C:3]([CH2:1][CH3:2])=[N:7][C:6]([I:8])=[C:5]12Participants
Procedure
According to the general procedure (GP10), microwave-assisted Pictet-Spengler reaction (60 W; 140° C.; 6.5 bars; 10 min.) between 2-(2-ethyl-4-iodo-imidazol-1-yl)-ethylamine (6.340 mmol) and 3-(2,5-difluoro-4-trifluoromethyl-phenyl)-propionaldehyde (1.509 g; 6.340 mmol) afforded 8-[2-(2,5-difluoro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-1-iodo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. LC-MS: tR=0.79 min.; [M+H]+=485.87 g/mol. Subsequent protection of the secondary amine, and purification by FC (DCM/MeOH=50/1) allowed the isolation of the pure product 8-[2-(2,5-difluoro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a slightly beige solid (1.890 g; 51%). LC-MS: tR=0.99 min.; [M+H]+=585.78 g/mol.
Sources & evidence
- ORD record
- ord-29f99ec5b36b4053a1b06b65e93d61e8
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188082B2
Reaction notes
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