HCID 53434400, compound → 8-[2-(3-Fluoro-4-trifluoromethyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine
Reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH3:10])[N:5]([CH2:7][CH2:8][NH2:9])[CH:6]=1.[F:11][C:12]1[CH:13]=[C:14]([CH2:22][CH2:23][CH:24]=O)[CH:15]=[CH:16][C:17]=1[C:18]([F:21])([F:20])[F:19]>>[F:11][C:12]1[CH:13]=[C:14]([CH2:22][CH2:23][CH:24]2[NH:9][CH2:8][CH2:7][N:5]3[C:4]([CH3:10])=[N:3][C:2]([I:1])=[C:6]23)[CH:15]=[CH:16][C:17]=1[C:18]([F:19])([F:20])[F:21]Participants
Procedure
According to the general procedure (GP10), microwave-assisted Pictet-Spengler reaction (60 W; 140° C.; 6.5 bars; 10 min.) between 2-(4-iodo-2-methyl-imidazol-1-yl)-ethylamine (51.840 mmol) and 3-(3-fluoro-4-trifluoromethyl-phenyl)-propionaldehyde (13.125 g; 59.616 mmol) afforded 8-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. LC-MS: tR=0.76 min.; [M+H]+=453.93 g/mol. Subsequent protection of the secondary amine, and purification by FC (DCM/MeOH=20/1) allowed the isolation of the pure product 8-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a pale yellow solid (15.450 g; 54%). LC-MS: tR=0.97 min.; [M+H]+=554.84 g/mol.
Sources & evidence
- ORD record
- ord-ee2b66f3eb2d47bd96529d8c366ccc23
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188082B2
Reaction notes
Loading…