4-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide → 4-[(7-Fluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

HRID 2238582Notes

Reaction equation

HRID 2238582 reaction equation
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=2[CH:5]=[C:4]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:3]=1.Cl[CH:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[O:22][CH2:21][CH2:20]1>>[F:29][C:25]1[CH:24]=[C:23]2[C:28]([CH:19]([O:1][C:2]3[C:10]4[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=4[CH:5]=[C:4]([C:13]([N:15]([CH3:16])[CH3:17])=[O:14])[CH:3]=3)[CH2:20][CH2:21][O:22]2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 534710164-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamideHCID 68689066HCID 68689066, compound

Product 1

HCID 159803194-[(7-Fluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamideYield 45%

Procedure

The title compound was prepared as a white solid in 45% yield (0.96 g) from 4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (1.3 g, 5.5 mmol, WO 2004054984) and 4-chloro-7-fluorochromane (2.0 g, 11 mmol, STEP 2) by the same manner in STEP 1 of Example 1:

Sources & evidence

ORD record
ord-14f98382fbd74b319fdcf9d9b89cc597
Source dataset
uspto-grants-2010_05
Patent number
US07718809B2

Reaction notes

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