HCID 66734063, compound → 3-Ethyl-8-(4-fluoro-3-trifluoromethyl-phenoxymethyl)-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:22]=[CH:21][C:16]([O:17][CH2:18][CH:19]=O)=[CH:15][C:14]=1[C:23]([F:26])([F:25])[F:24]>>[CH2:1]([C:3]1[N:4]2[CH2:9][CH2:10][NH:11][CH:19]([CH2:18][O:17][C:16]3[CH:21]=[CH:22][C:13]([F:12])=[C:14]([C:23]([F:26])([F:24])[F:25])[CH:15]=3)[C:5]2=[C:6]([I:8])[N:7]=1)[CH3:2]Participants
3
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 (1.540 mmol) and (4-fluoro-3-trifluoromethyl-phenoxy)-acetaldehyde (0.342 g; 1.540 mmol) afforded 3-ethyl-8-(4-fluoro-3-trifluoromethyl-phenoxymethyl)-1-iodo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. Subsequent protection of the secondary amine, and purification by FC (DCM/MeOH=60/1) allowed the isolation of the pure product 3-ethyl-8-(4-fluoro-3-trifluoromethyl-phenoxymethyl)-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow solid (0.412 g; 47%). LC-MS: tR=0.93 min.; [M+H]+=570.37 g/mol.
Sources & evidence
- ORD record
- ord-fe5aca68bbd343559faff91930bfe588
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188082B2
Reaction notes
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