2-(4-Iodo-2-methyl-imidazol-1-yl)-ethylamine → HCID 66733870, compound

HRID 1929655Notes

Reaction equation

HRID 1929655 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]([CH2:20][CH2:21][CH:22]=O)[CH:15]=[C:16]([F:19])[C:17]=1[CH3:18]>>[F:11][C:12]1[CH:13]=[C:14]([CH2:20][CH2:21][CH:22]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]=[C:16]([F:19])[C:17]=1[CH3:18]

Participants

3

Reactant 2

HCID 667339802-(4-Iodo-2-methyl-imidazol-1-yl)-ethylamineHCID 730140753-(3,5-Difluoro-4-methylphenyl)propionaldehyde

Product 1

HCID 66733870HCID 66733870, compound

Procedure

According to the general procedure (GP10), the microwave-assisted Pictet-Spengler reaction (60 W; 110° C.; 5 bars; 10 min.) between 2-(4-iodo-2-methyl-imidazol-1-yl)-ethylamine (696 mg; 2.774 mmol) and 3-(3,5-difluoro-4-methyl-phenyl)-propionaldehyde (510 mg; 2.774 mmol) afforded 8-[2-(3,5-difluoro-4-methyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine which was Boc-protected and finally purified by FC (DCM/MeOH=25/1).

Sources & evidence

ORD record
ord-0f58c94c0e474048974b1b7f0dbf4277
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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