Sodium Hypochlorite → HCID 86675907, compound

HRID 572650Notes

Reaction equation

HRID 572650 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[C:13]([CH:15]=[N:16][OH:17])[N:12]=[C:11]([CH3:18])[N:10]=1)=[O:8].[CH3:23][N:24]1[CH:29]=[C:28]([CH:30]=[CH2:31])[CH:27]=[CH:26][C:25]1=[O:32].Cl[O-].[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[C:13]([C:15]2[CH2:31][CH:30]([C:28]3[CH:27]=[CH:26][C:25](=[O:32])[N:24]([CH3:23])[CH:29]=3)[O:17][N:16]=2)[N:12]=[C:11]([CH3:18])[N:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 23665760Sodium HypochloriteHCID 68559883HCID 68559883, compoundHCID 136413232HCID 136413232, compound

Product 1

HCID 86675907HCID 86675907, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3,4-difluorobenzyl)-6-((hydroxyimino)methyl)-2-methylpyrimidine-4-carboxamide (13.60 g, 44.4 mmol, Preparation #A.1.2) and 1-methyl-5-vinylpyridin-2(1H)-one (6 g, 44.4 mmol, Preparation #F.1.13) in DCM (150 mL) was added 9% aqueous sodium hypochlorite solution (80 mL, 1296 mmol, Avra labs) drop wise at 10-15° C. for about 30 min. Reaction mixture was allowed to stir for another 15-30 min, diluted the reaction mixture with water (100 mL) and the product extracted with DCM (2×100 mL). The combined organic layers was dried over sodiumsulphate and evaporated to dryness. The resulting crude material was purified by silica gel column chromatography by eluting with 2% methanol in DCM. Relevant fractions containing product were combined and evaporated under reduced pressure to afford N-(3,4-difluorobenzyl)-2-methyl-6-(5-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide 3 g (15.38%) as pale yellow solid; 1H NMR (400 MHz, DMSO): δ 9.606-9.574 (m, 1H), 8.179 (s, 1H), 7.872-7.866 (d, J=2.4 Hz, 1H), 7.527-7.497 (dd, J=9.6 Hz, 1H), 7.421-7.353 (m, 2H), 7.205-7.173 (m, 1H), 6.436-6.412 (d, J=9.6 Hz, 1H), 5.688-5.637 (m, 1H), 4.504-4.488 (d, J=6.4 Hz, 2H), 3.836-3.764 (m, 1H), 3.463-3.440 (m, 1H), 3.425 (s, 3H), 2.767 (s, 3H); MS m/z: 440.2 (M+H)+.

Workup

  1. customReaction mixture
  2. extractionthe product extracted with DCM (2×100 mL)
  3. dry with materialThe combined organic layers was dried over sodiumsulphate
  4. customevaporated to dryness
  5. customThe resulting crude material was purified by silica gel column chromatography
  6. washby eluting with 2% methanol in DCM
  7. additionRelevant fractions containing product
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fe1ef9630bd744b98139c7f6945ebf11
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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