Azetidine hydrochloride → 6-(Azetidin-1-ylcarbonyl)-4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-1,2-dimethyl-1H-benzimidazole

HRID 2238596Notes

Reaction equation

HRID 2238596 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])[N:19]([CH3:24])[C:18]=3[CH:17]=[C:16]([C:25]([OH:27])=O)[CH:15]=1)[CH2:5][CH2:6][O:7]2.Cl.[NH:29]1[CH2:32][CH2:31][CH2:30]1>>[N:29]1([C:25]([C:16]2[CH:15]=[C:14]([O:13][CH:4]3[C:3]4[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=4[F:1])[O:7][CH2:6][CH2:5]3)[C:22]3[N:21]=[C:20]([CH3:23])[N:19]([CH3:24])[C:18]=3[CH:17]=2)=[O:27])[CH2:32][CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 12308726Azetidine hydrochlorideHCID 686901324-[(5,7-Difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-1,2-dimethyl-1H-benzimidazole-6-carboxylic acid

Product 1

HCID 593038956-(Azetidin-1-ylcarbonyl)-4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-1,2-dimethyl-1H-benzimidazoleYield 80%

Procedure

The title compound was prepared as a colorless amorphous in 80% yield (1.4 g) from 4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-1,2-dimethyl-1H-benzimidazole-6-carboxylic acid (1.6 g, 4.2 mmol, STEP 2 of Example 19) and azetidine hydrochloride (0.79 g, 8.4 mmol) by the same manner in STEP 3 of Example 11.

Sources & evidence

ORD record
ord-3f7b8caaea4f48d193e07f92e760fab5
Source dataset
uspto-grants-2010_05
Patent number
US07718809B2

Reaction notes

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