Sodium Hydroxide → HCID 16727476, compound

HRID 1280101Notes

Reaction equation

HRID 1280101 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([NH:18][NH2:19])=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:20]2[CH:24]=[CH:23][O:22][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:26][C:27](=[O:37])[C:28]1[CH:33]=[CH:32][C:31]([C:34](Cl)=[O:35])=[CH:30][CH:29]=1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C.CC(O)=O>[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([NH:18][NH:19][C:34]([C:31]4[CH:32]=[CH:33][C:28]([C:27]([OH:37])=[O:26])=[CH:29][CH:30]=4)=[O:35])=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:20]2[CH:24]=[CH:23][O:22][CH:21]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 233781581H-Benzimidazole-5-carboxylic acid, 1-cyclohexyl-2-(3-furanyl)-, hydrazide

Product 1

HCID 16727476HCID 16727476, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

1-Cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carboxylic acid hydrazide (0.022 g, 0.068 mmol) and methyl-4-chlorocarbonylbenzoate (0.013 g, 0.068 mmol) were stirred in DMF (1 mL) in the presence of DIEA (0.018 g, 0.14 mmol) for 2 h. An aqueous solution of NaOH (2.5 N, 0.22 mL, 0.55 mmol) was then added and the mixture was stirred for 2 h at room temperature. The reaction mixture was acidified by the addition of AcOH and purified by reversed phase C18 preparative HPLC to give the title compound of example 143.

Workup

  1. custompurified by reversed phase C18 preparative HPLC

Sources & evidence

ORD record
ord-b185259328b046feb2d4c0abbdc7b923
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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