Acetic Anhydride → HCID 178474884, compound

HRID 2282224Notes

Reaction equation

HRID 2282224 reaction equation
Cl.Cl.[CH3:3][C:4]1[C:16]([C:17]2[S:18][C:19]([C:28]3[N:32]=[CH:31][NH:30][N:29]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:21]=2)=[C:7]2[CH:8]=[C:9]([O:12][CH2:13][CH2:14][NH2:15])[CH:10]=[CH:11][N:6]2[N:5]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].C(=O)(O)[O-].[Na+].CCOC(C)=O>C1COCC1>[CH3:3][C:4]1[C:16]([C:17]2[S:18][C:19]([C:28]3[N:32]=[CH:31][NH:30][N:29]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:21]=2)=[C:7]2[CH:8]=[C:9]([O:12][CH2:13][CH2:14][NH:15][C:33](=[O:35])[CH3:34])[CH:10]=[CH:11][N:6]2[N:5]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178433763HCID 178433763, compound

Product 1

HCID 178474884HCID 178474884, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-({2-methyl-3-[4-phenyl-5-(1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyridin-5-yl}oxy)ethanamine di-hydrochloride (100 mg, 0.20 mmol) obtained in Example 73-B(i) and TEA (0.75 mL) in THF (10 mL), was added acetic anhydride (0.5 mL, 5.3 mmol) at 0° C., and the mixture was stirred at 0° C. for 1 h. To the reaction mixture were added saturated aqueous solution of sodium bicarbonate (50 mL) and EtOAc (50 mL), and the mixture was stirred for 30 min. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was washed with EtOAc and diisopropyl ether, and dried to give the title compound (33 mg, 35%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. washThe residue was washed with EtOAc and diisopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-a4f452e7cb0f4120933aad4b09033984
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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