m-Chloroperbenzoic acid → N-(3-Chlorophenyl)-1-methyl-7-[(1-oxido-4-thiomorpholinyl)carbonyl]-1H-pyrrolo[3,2-c]pyridin-4-amine hydrochloride

HRID 733728Notes

Reaction equation

HRID 733728 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N:17]([CH3:18])[C:13]=3[C:12]([C:19]([N:21]3[CH2:26][CH2:25][S:24][CH2:23][CH2:22]3)=[O:20])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:32]>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N:17]([CH3:18])[C:13]=3[C:12]([C:19]([N:21]3[CH2:22][CH2:23][S:24](=[O:32])[CH2:25][CH2:26]3)=[O:20])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57841005N-(3-Chlorophenyl)-1-methyl-7-(4-thiomorpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine

Product 1

HCID 68869671N-(3-Chlorophenyl)-1-methyl-7-[(1-oxido-4-thiomorpholinyl)carbonyl]-1H-pyrrolo[3,2-c]pyridin-4-amine hydrochlorideYield 147.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3-chlorophenyl)-1-methyl-7-(4-thiomorpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine (100 mg) in DCM (3 ml) was cooled to −78 C and meta-chloroperoxybenzoic acid (58 mg) was added and the reaction stirred under argon for 30 minutes. The reaction was partitioned between dichloromethane and water and the organic layer separated. The organic layer was then washed three times with water, aqueous sodium sulfite solution, dried (Na2SO4) and evaporated. The residue was purified by MDAP to afford the free base as a white solid (84 mg). This was dissolved in methanol and a solution of 11.0M hydrochloric acid in diethyl ether (0.5 ml) and after evaporation afforded the title compound as a white solid (85 mg).

Workup

  1. additionwas added
  2. customThe reaction was partitioned between dichloromethane and water
  3. customthe organic layer separated
  4. washThe organic layer was then washed three times with water, aqueous sodium sulfite solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-23502a056a814b3bbc5488bbc1b8e82d
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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