Isobutyryl chloride → HCID 46836496, compound

HRID 2366502Notes

Reaction equation

HRID 2366502 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[S:15][C:16]2[CH2:24][CH2:23][C:22]3[NH:21][N:20]=[CH:19][C:18]=3[C:17]=2[N:25]=1>C1COCC1>[CH3:3][CH:2]([CH3:4])[C:1]([N:21]1[C:22]2[CH2:23][CH2:24][C:16]3[S:15][C:14]([NH:13][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=4)=[N:25][C:17]=3[C:18]=2[CH:19]=[N:20]1)=[O:5]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 46700737HCID 46700737, compound

Product 1

HCID 46836496HCID 46836496, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 5: Isobutyryl chloride (0.37 mmol, 39 μL) was added dropwise to a solution of N-(pyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine (0.37 mmol, 100 mg) in THF (2 mL) and the reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was quenched with a saturated solution of NaHCO3 and the aqueous phase was extracted with DCM. The organic phase was dried over Na2SO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM as eluent to yield after evaporation 2-methyl-1-(2-(pyridin-2-ylamino)-4H-thiazolo[4,5-e]indazol-6(5H)-yl)propan-1-one

Workup

  1. customThe reaction mixture was quenched with a saturated solution of NaHCO3
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationwas filtered
  5. concentrationwas concentrated
  6. customThe resulting crude product was purified by flash chromatography over silica gel
  7. customto yield
  8. customafter evaporation 2-methyl-1-(2-(pyridin-2-ylamino)-4H-thiazolo[4,5-e]indazol-6(5H)-yl)propan-1-one

Sources & evidence

ORD record
ord-0521b01325eb4c0b9740b376a3f256ae
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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