4-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide → 4-[(5-Fluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

HRID 2238585Notes

Reaction equation

HRID 2238585 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][CH:25]=[CH:26][C:27]=2[F:29])[O:22][CH2:21][CH2:20]1>>[F:29][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:28]=1[CH:19]([O:1][C:2]1[C:10]3[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=3[CH:5]=[C:4]([C:13]([N:15]([CH3:16])[CH3:17])=[O:14])[CH:3]=1)[CH2:20][CH2:21][O:22]2

Participants

3

Reactant 2

HCID 534710164-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamideHCID 686876584-Chloro-5-fluorochromane

Product 1

HCID 593038894-[(5-Fluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamideYield 35%

Procedure

The title compound was prepared as a pale brown solid in 35% yield (69 mg) from 4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (120 mg, 0.51 mmol, WO 2004054984) and 4-chloro-5-fluorochromane (100 mg, 0.54 mmol, STEP 2) by the same manner in STEP 1 of Example 1:

Sources & evidence

ORD record
ord-3e316f7951f141829150fffe8b4ac511
Source dataset
uspto-grants-2010_05
Patent number
US07718809B2

Reaction notes

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