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

HRID 2239317Notes

Reaction equation

HRID 2239317 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.Cl.[NH:28]1[CH2:31][CH2:30][CH2:29]1>>[N:28]1([C:24]([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])[NH:19][C:18]=3[CH:17]=2)=[O:26])[CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 12308726Azetidine hydrochlorideHCID 685745597-[(5,7-Difluorochroman-4-yl)oxy]-2-methyl-1H-benzo[d]imidazole-5-carboxylic Acid

Product 1

HCID 58900200(-)-6-(Azetidin-1-ylcarbonyl)-4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-2-methyl-1H-benzimidazole

Procedure

The title compound was prepared as a white solid (132 mg, 79%) from (−)-4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-2-methyl-1H-benzimidazole-6-carboxylic acid (150 mg, STEP 1) and azetidine hydrochloride (117 mg, 1.25 mmol) by the same manner in STEP 5 of Example 1.

Sources & evidence

ORD record
ord-9003eb1eaa6c45979eca0c48ee40088b
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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