Ethoxalyl chloride → HCID 58541957, compound

HRID 1966744Notes

Reaction equation

HRID 1966744 reaction equation
[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([O:20][CH3:21])[CH:19]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([NH:27][OH:28])=[NH:26])([CH3:4])([CH3:3])[CH3:2].[CH2:32]([O:34][C:35](=[O:39])[C:36](Cl)=O)[CH3:33].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:32]([O:34][C:35]([C:36]1[O:28][N:27]=[C:25]([C:24]2[CH:29]=[CH:30][CH:31]=[C:22]([C:6]3[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:9]4[CH:10]=[CH:11][C:12]([C:14]5[CH:15]=[N:16][CH:17]=[C:18]([O:20][CH3:21])[CH:19]=5)=[CH:13][C:8]=4[N:7]=3)[CH:23]=2)[N:26]=1)=[O:39])[CH3:33]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 81531DiisopropylethylamineHCID 178493720HCID 178493720, compound

Product 1

HCID 58541957HCID 58541957, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[1-tert-Butyl-5-(5-methoxy-pyridin-3-yl)-1H-benzimidazol-2-yl]-N-hydroxy-benzamidine (0.500 g, 1.20 mmol) is dissolved in DMF (5 mL). Chloro-oxo-acetic acid ethyl ester (0.177 g, 1.30 mmol) is added followed by diisopropyl-ethylamine (1.5 mL). The reaction mixture is stirred at room temperature for 2 hours then heated at 110° C. for 16 hours. The solvent is removed in vacuum. The residue is purified by flash chromatography (silica gel 40 g, eluted with 0-100% ethyl acetate in hexane) to give the title compound (0.454 g, 76%). LCMS (ESMS): m/z 498.61 (M++1).

Workup

  1. temperaturethen heated at 110° C. for 16 hours
  2. customThe solvent is removed in vacuum
  3. customThe residue is purified by flash chromatography (silica gel 40 g, eluted with 0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-38569557797b41e7894bb553716c3503
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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