Triethylamine → HCID 178489256, compound

HRID 423200Notes

Reaction equation

HRID 423200 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:32](O)=[O:33])[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(Cl)(=O)OCC.[BH4-].[Na+]>O.CO.C1COCC1>[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]([CH2:32][OH:33])[CH:28]=4)=[CH:23][CH:22]=3)[C:10](=[O:35])[C:7]=2[NH:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 178489257HCID 178489257, compound

Product 1

HCID 178489256HCID 178489256, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

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 (0.080 g, 0.17 mmol), triethylamine (0.031 mL, 0.22 mmol) and THF (2 mL), ethyl chlorocarbonate (0.019 mL, 0.20 mmol) was added under ice-cooling conditions and the mixture stirred at r.t. for 2 hr. Sodium borohydride (0.026 g, 0.68 mmol), water (0.3 mL) and methanol (1 mL) were added to the mixture and the mixture was stirred at r.t. for 10 min. Water was added to the mixture, the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from dichloromethane, diethyl ether and ethyl acetate, and the precipitate was collected by filtration to give 3-t-butyl-5-[4-(3-hydroxymethyl-5-isoxazolyl)-phenyl]-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one (0.068 g, 88%) as colorless crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling conditions
  3. stirringthe mixture was stirred at r.t. for 10 min
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with 1N hydrochloric acid, saturated sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from dichloromethane, diethyl ether and ethyl acetate
  9. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c453e90954fd4bdc895340465945e7ca
Source dataset
uspto-grants-2012_01
Patent number
US08101644B2

Reaction notes

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