Dichloromethane → HCID 22387965, compound

HRID 1072882Notes

Reaction equation

HRID 1072882 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18].[Cl:28]N1C(=O)CCC1=O.ClCCl>C(O)(=O)C>[Cl:1][C:2]1[CH:22]=[C:21]([C:23]2[S:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31398Chlorosuccinimide2×HCID 22388456HCID 22388456, compound

Product 1

HCID 22387965HCID 22387965, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of methyl 3-[2-chloro-4-(thiophen-2-yl)benzyl]-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (50 mg, 0.126 mmol) in acetic acid (1 ml) was added N-chlorosuccinimide (19 mg, 0.138 mmol) at room temperature. Thirty minutes later, dichloromethane (0.5 ml) was added to the reaction mixture to give a clear transparent solution. Four hours later, N-chlorosuccinimide (19 mg, 0.138 mmol) was further added. The reaction mixture was left standing overnight and concentrated. The residue was purified by p-TLC (chloroform/methanol=40/1) to give the object compound (52 mg, 95.7%) as a colorless oil.

Workup

  1. customto give a clear transparent solution
  2. waitThe reaction mixture was left
  3. concentrationconcentrated
  4. customThe residue was purified by p-TLC (chloroform/methanol=40/1)

Sources & evidence

ORD record
ord-5a8cfe0067774a0295f3d10859cb9ce3
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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