Ethyl Acetate → HCID 11647780, compound

HRID 550571Notes

Reaction equation

HRID 550571 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:12]=[N:11][NH:10][C:9]=1[NH2:13])=[O:7].CN(C)[CH:16]=[CH:17][C:18]([C:20]1[CH:21]=[C:22]([N:26]([CH2:31][C:32]#[CH:33])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:24][CH:25]=1)=O.C(OCC)(=O)C>C(O)(=O)C>[CH2:31]([N:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:18]2[N:10]3[N:11]=[CH:12][C:8]([C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[O:7])=[C:9]3[N:13]=[CH:16][CH:17]=2)[CH:21]=1)[S:27]([CH3:30])(=[O:29])=[O:28])[C:32]#[CH:33]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11550150(5-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanoneHCID 86761316HCID 86761316, compound

Product 1

HCID 11647780HCID 11647780, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.1 g (0.33 mmol) of 4-thiophene-2-carbonyl-2H-pyrazol-3-ylamine and 0.063 g (0.33 mmol) of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-2-propynyl-methanesulfonamide were dissolved in 10 ml of glacial acetic acid. After refluxing for 8 hours, the solvent was removed by reduced pressure distillation. To the resultant residue 10 ml of dichloromethane and 10 ml of a saturated solution of sodium bicarbonate were added. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporate to dryness to yield an oil which, in the presence of ethyl acetate gave a yellow solid, 111 mg (yield=78%) N-2-propynyl-N-{3-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-methanesulfonamide.

Workup

  1. temperatureAfter refluxing for 8 hours
  2. customthe solvent was removed by reduced pressure distillation
  3. additionTo the resultant residue 10 ml of dichloromethane and 10 ml of a saturated solution of sodium bicarbonate were added
  4. customThe two layers were separated
  5. washthe aqueous layer was washed with 10 ml of dichloromethane
  6. washThe organic layers were washed with 10 ml of water
  7. dry with materialdried over magnesium sulfate
  8. customThe dichloromethane layer was evaporate to dryness
  9. customto yield an oil which

Sources & evidence

ORD record
ord-efc60ac5ac7548638b156a4405c45033
Source dataset
uspto-grants-2011_05
Patent number
US07947688B2

Reaction notes

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