Pivaloyl chloride → HCID 178468557, compound

HRID 1410197Notes

Reaction equation

HRID 1410197 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:24]([Cl:25])=[CH:23][C:9]2[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH2:20][NH2:21])[CH:17]=[CH:16][C:15]=3[Cl:22])[NH:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:24]([Cl:25])=[CH:23][C:9]2[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH2:20][NH:21][C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:31])[CH:17]=[CH:16][C:15]=3[Cl:22])[NH:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178468556HCID 178468556, compound

Product 1

HCID 178468557HCID 178468557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Ethyl-2-[5-(aminomethyl)-2-chlorophenylamino]-6-chloro-benzimidazole-5-carboxylate (1.00 g, 2.4 mmol), pivaloyl chloride (0.296 ml, 2.4 mmol), 1.5 ml TEA and 50 ml THF were stirred for 18 h at rt. The mixture was concentrated, diluted with EtOAc, washed 2× with H2O, dried over Na2SO4 and concentrated. The residue was purified by chromatography to give the sub-title compound. Yield 0.92 g (83%).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed 2× with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-da8a8a6073044723adf550d31ce96951
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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