4-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide → 4-(3,4-Dihydro-1H-isochromen-4-yloxy)-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

HRID 2238586Notes

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][CH:27]=2)[CH2:22][O:21][CH2:20]1>>[CH2:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]([O:1][C:2]2[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]=2)[CH2:20][O:21]1

Participants

Reactant 2

HCID 534710164-Hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide

HCID 686884094-Chloroisochroman

Product 1

HCID 593038914-(3,4-Dihydro-1H-isochromen-4-yloxy)-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamideYield 12%

Procedure

The title compound was prepared as a white solid in 12% yield (38 mg) from 4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide (0.20 g, 0.85 mmol, WO 2004054984) and 4-chloro-3,4-dihydro-1H-isochromene (0.20 g, 1.2 mmol, STEP 1) by the same manner in STEP 1 of Example 1:

Sources & evidence

ORD record: ord-d8b1309e774c46b3b62c016aa4c1ac79
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718809B2

Reaction notes

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