Dimethylformamide → HCID 178489261, compound

HRID 455960Notes

Reaction equation

HRID 455960 reaction equation
[C:1]([C:5]1[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][N:30]=[C:29](C(O)=O)[CH:28]=4)=[CH:23][CH:22]=3)[C:10](=[O:35])[C:7]=2[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C[N:44]([CH:46]=[O:47])C.[C:48]([OH:52])([CH3:51])([CH3:50])[CH3:49]>>[C:1]([C:5]1[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[O:31][N:30]=[C:29]([O:52][C:48]([CH3:51])([CH3:50])[CH3:49])[C:28]=4[N:44]=[C:46]=[O:47])=[CH:23][CH:22]=3)[C:10](=[O:35])[C:7]=2[NH:8][N:9]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6386tert-ButanolHCID 8471TriethylamineHCID 178489257HCID 178489257, compound

Product 1

HCID 178489261HCID 178489261, compoundYield 52%

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-t-butyl-5-[4-(3-carboxy-5-isoxazolyl)phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.948 g, 2.0 mmol), triethylamine (0.33 mL, 2.4 mmol) and DMF (15 mL), diphenyl phosphorylazido (0.52 mL, 2.4 mmol) was added, and the mixture was stirred at 60° C. for 2 hr. Then, t-butanol (15 mL) and molecular sieve powder 4 A (2 g) was added and the mixture was stirred at 90° C. for 3 hr. Insoluble matter was removed by filtration, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous ammonium chloride and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from dichloromethane to give 3-t-butyl-5-[4-(3-t-butoxy-carbonylamino-5-isoxazolyl)phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.566 g, 52%) as colorless crystals.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 90° C. for 3 hr
  3. customInsoluble matter was removed by filtration, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with aqueous ammonium chloride and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from dichloromethane

Sources & evidence

ORD record
ord-0ba4879c15294dffa7bf0804351075ff
Source dataset
uspto-grants-2013_07
Patent number
US08497263B2

Reaction notes

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