Pyrrolidine → 4-[(5,7-Difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-2-methyl-6-(pyrrolidin-1-ylcarbonyl)-1H-benzimidazole

HRID 2239307Notes

Reaction equation

HRID 2239307 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.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[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:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:26])[CH:15]=1)[CH2:5][CH2:6][O:7]2

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 685745597-[(5,7-Difluorochroman-4-yl)oxy]-2-methyl-1H-benzo[d]imidazole-5-carboxylic Acid

Product 1

HCID 162022704-[(5,7-Difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-2-methyl-6-(pyrrolidin-1-ylcarbonyl)-1H-benzimidazoleYield 56%

Procedure

The title compound was prepared as a white solid (70 mg, 56% 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) and pyrrolidine (59 mg, 0.832 mmol) by the same manner in STEP 5 of Example 1.

Sources & evidence

ORD record
ord-485ef3d65a6b42369869ce725405882b
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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