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m-Chloroperbenzoic acid → HCID 9868455, compound

HRID 1835137
Notes
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Reaction equation

HRID 1835137 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:7]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[CH:8]=[C:9]2[C:14]([CH2:15][CH:16]([CH3:18])[CH3:17])=[N:13][N:12]([CH3:19])[C:11](=[O:20])[C:10]=12.ClC1C=C(C=CC=1)C(OO)=[O:37].C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl>[OH:1][CH2:2][CH2:3][CH2:4][S:5]([C:6]1[N:7]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[CH:8]=[C:9]2[C:14]([CH2:15][CH:16]([CH3:18])[CH3:17])=[N:13][N:12]([CH3:19])[C:11](=[O:20])[C:10]=12)=[O:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 656671Sodium PyrosulfiteHCID 5282542Mct1-IN-2

Product 1

HCID 9868455HCID 9868455, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

2,6-Dihydro-7-[(3-hydroxypropyl)thio]-2-methyl-4-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1-one (0.34 g) prepared as described in Example 3 above was dissolved in dichloromethane (7 ml) and 3-chloroperoxybenzoic acid (229 mg) was added. After 4 hours sodium bicarbonate (aqueous) and sodium metabisulfite (aqueous) were added and the mixture was extracted thrice with dichloromethane. The combined organic extracts were washed with brine, dried, filtered and evaporated. The residue was chromatographed eluting with ethyl acetate and then ethyl acetate:ethanol (19:1-9:1) to give 2 products. The more polar product was triturated with ether to give 2,6-Dihydro-7-[(3-hydroxypropyl)sulfinyl]-2-methyl-4(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1-one (A) (48 mg) whilst the less polar product was recrystallised from isohexane-ethyl acetate to give 2,6-dihydro-7-[(3-hydroxypropyl)sulfonyl]-2-methyl-4-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1-one (B) (94 mg).

Workup

  1. extractionthe mixture was extracted thrice with dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed
  7. washeluting with ethyl acetate
  8. customethyl acetate:ethanol (19:1-9:1) to give 2 products
  9. customThe more polar product was triturated with ether

Sources & evidence

ORD record
ord-522006e159ae4fb19fb2cf9e350c715c
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06770646B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes