3-[4-(Trifluoromethyl)phenyl]propanal → 1-Iodo-3-methoxymethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine

HRID 1929656Notes

Reaction equation

HRID 1929656 reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH2:10][O:11][CH3:12])[N:5]([CH2:7][CH2:8][NH2:9])[CH:6]=1.[F:13][C:14]([F:26])([F:25])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]=O)=[CH:17][CH:16]=1>>[I:1][C:2]1[N:3]=[C:4]([CH2:10][O:11][CH3:12])[N:5]2[CH2:7][CH2:8][NH:9][CH:23]([CH2:22][CH2:21][C:18]3[CH:19]=[CH:20][C:15]([C:14]([F:13])([F:25])[F:26])=[CH:16][CH:17]=3)[C:6]=12

Participants

3

Reactant 2

HCID 216838073-[4-(Trifluoromethyl)phenyl]propanalHCID 667336042-(4-Iodo-2-methoxymethyl-imidazol-1-yl)-ethylamine

Product 1

HCID 667340801-Iodo-3-methoxymethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine

Procedure

According to the general procedure (GP10), the microwave-assisted Pictet-Spengler reaction (60 W; 95° C.; 9 bars; 10 min.) between 2-(4-iodo-2-methoxymethyl-imidazol-1-yl)-ethylamine (596 mg; 2.119 mmol) and 3-(4-trifluoromethyl-phenyl)-propionaldehyde (428 mg; 2.119 mmol) afforded 1-iodo-3-methoxymethyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine which was Boc-protected and finally purified by FC (DCM/MeOH=30/1).

Sources & evidence

ORD record
ord-d8f3f470658a4499b8176924a58d3dde
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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