m-Chloroperbenzoic acid → HCID 178479968, compound

HRID 1948126Notes

Reaction equation

HRID 1948126 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:6]=2[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:21])C=1>CC(C)=O>[NH2:1][C:2]1[C:7]2[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:6]=2[CH:5]=[CH:4][N+:3]=1[O-:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 672535394-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one2×

Product 1

HCID 178479968HCID 178479968, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one (Compound 310B, 62.5 mg, 0.383 mmol) and m-Chloroperbenzoic acid (145 mg, 0.843 mmol) in Acetone (10.0 mL) was stirred at rt for 90 minutes. The reaction mixture was concentrated under reduced pressure to an off white solid. The crude material was purified by silica gel chromatography on the combi-flash Rf system using DCM/7 N NH3 in MeOH (100:0→90:10) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a white solid (68.3 mg, 99.5%). 1H NMR (DMSO-d6, 400 MHz): δ=8.19 (d, J=6.57 Hz, 1H), 7.02 (br. s., 2H), 6.82 (d, J=6.57 Hz, 1H), 4.41 (s, 2H), 3.01 (s, 3H). MS (ES+): m/z 180.07 [MH+] (TOF, polar).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to an off white solid
  2. customThe crude material was purified by silica gel chromatography on the combi-flash Rf system
  3. additionThe fractions containing product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-099f70ded5f24dd5afb6b7a996804090
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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