1,2-Ethanediamine, N1,N1,N2-trimethyl- → 4-[(5,7-Difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N-[2-(dimethylamino)ethyl]-N,2-dimethyl-1H-benzimidazole-6-carboxamide

HRID 2239309Notes

Reaction equation

HRID 2239309 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]([O:13][C:14]1[C:22]3[N:21]=[C:20]([CH3:23])[NH:19][C:18]=3[CH:17]=[C:16]([C:24]([OH:26])=O)[CH:15]=1)[CH2:5][CH2:6][O:7]2.[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][NH:31][CH3:32]>>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]([O:13][C:14]1[C:22]3[N:21]=[C:20]([CH3:23])[NH:19][C:18]=3[CH:17]=[C:16]([C:24]([N:31]([CH2:30][CH2:29][N:28]([CH3:33])[CH3:27])[CH3:32])=[O:26])[CH:15]=1)[CH2:5][CH2:6][O:7]2

Participants

3

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 685745597-[(5,7-Difluorochroman-4-yl)oxy]-2-methyl-1H-benzo[d]imidazole-5-carboxylic Acid

Product 1

HCID 589001974-[(5,7-Difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N-[2-(dimethylamino)ethyl]-N,2-dimethyl-1H-benzimidazole-6-carboxamideYield 13%

Procedure

The title compound was prepared as a white solid (10 mg, 13% yield for 3 steps) from 4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-2-methyl-1H-benzimidazole-6-carboxylic acid (100 mg, crude, STEP 4 in Example 4) and N,N,N′-trimethyl-1,2-ethanediamine (45 mg, 0.44 mmol) by the same manner in STEP 5 of Example 1.

Sources & evidence

ORD record
ord-f97bf719ed8740eb9c19bdd8c3cb8339
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

Loading…