Triethylamine → 6-(3-Methoxy-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole

HRID 38100Notes

Reaction equation

HRID 38100 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:12]3[S:13][CH2:14][CH:15](O)[N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>C(COC)OC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:12]3[S:13][CH:14]=[CH:15][N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 674238586-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-3-ol

Product 1

HCID 674234366-(3-Methoxy-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazoleYield 61%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude 6-(3-methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-3-ol (120 mg, 0.369 mmol) was dissolved in dry dimethoxyethane (2 mL) under nitrogen. Trifluoroacetic anhydride (0.200 mL, 1.416 mmol, 3.8 eq) and triethylamine (0.100 mL, 0.718 mmol, 2 eq) were added and the mixture was stirred at room temperature for 20 hours. The solution was then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine, dried and evaporated to dryness. The crude product was purified by chromatography on silica gel (eluant: DCM/MeOH 97:3) to give 69 mg (61%) of 6-(3-methoxy-phenyl)-7-pyridin-4-yl-pyrazolo[5,1-b]thiazole as white solid.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. customevaporated to dryness
  4. customThe crude product was purified by chromatography on silica gel (eluant: DCM/MeOH 97:3)

Sources & evidence

ORD record
ord-c510a242b56c412a91084030a50f6953
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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