Acetic Acid → HCID 66646088, compound

HRID 1695502Notes

Reaction equation

HRID 1695502 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:3]=1[CH:13]=O.Cl.[CH2:16]([O:18][C:19]([C:21]1[N:22]([CH3:27])[N:23]=[C:24]([NH2:26])[CH:25]=1)=[O:20])[CH3:17].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:27][N:22]1[C:21]([C:19]([O:18][CH2:16][CH3:17])=[O:20])=[CH:25][C:24]([NH:26][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:23]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 451568431197228-34-4HCID 867615585-Methyl-3-(2-pyridinyl)-4-isoxazolecarboxaldehyde

Product 1

HCID 66646088HCID 66646088, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-methyl-3-(pyridin-2-yl)isoxazole-4-carbaldehyde (811 mg, 4.31 mmol) and 5-amino-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester hydrochloride (886 mg, 4.31 mmol) in MeOH (36 mL) was added molecular sieves (1.3 g). The reaction mixture was stirred at RT for 1 h. Then acetic acid (3.45 mL, 60.3 mmol) was added. After stirring for additional 5 min, sodium cyanoborohydride (542 mg, 8.62 mmol) was added in portions over 2 min and the reaction mixture was stirred at RT for 30 min, then evaporated. The residue was extracted with dichloromethane and then washed with a saturated solution of sodium hydrogen carbonate. The organic layers were washed with water and brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, dichloromethane) afforded the title compound as a white solid (814 mg, 55%). MS: m/e=342.1 [M+H]+.

Workup

  1. additionwas added molecular sieves (1.3 g)
  2. stirringAfter stirring for additional 5 min
  3. stirringthe reaction mixture was stirred at RT for 30 min
  4. customevaporated
  5. extractionThe residue was extracted with dichloromethane
  6. washwashed with a saturated solution of sodium hydrogen carbonate
  7. washThe organic layers were washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customPurification by chromatography (silica, dichloromethane)

Sources & evidence

ORD record
ord-18813eae668b477485a47e0095c3bcc4
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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