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Chloroacetaldehyde → 6-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-3-ol

HRID 38099
Notes
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Reaction equation

HRID 38099 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]([SH:14])[NH:12][N:13]=2)[CH:6]=[CH:7][CH:8]=1.Cl[CH2:22][CH:23]=[O:24]>C1COCC1.O.C(OC(=O)C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:11]3[S:14][CH2:22][CH:23]([OH:24])[N:12]3[N:13]=2)[CH:6]=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 33ChloroacetaldehydeHCID 178489941HCID 178489941, compound

Product 1

HCID 674238586-(3-Methoxy-phenyl)-7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-3-olYield 93%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

5-(3-Methoxy-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol prepared as described in Example 8 (115 mg, 0.406 mmol) was dissolved in a 1:1 THF/water mixture (3 mL). A 55% aqueous solution of chloroacetaldehyde (0.071 mL, 0.609 mmol, 1.5 eq) was added and the mixture was stirred at room temperature for 2 hours. It was then diluted with ethylacetate and washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and evaporated to dryness to give 123 mg (93%) of crude product, which was used without further purification in the following step.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-c64852dab9d24bf9bd55b39536960b19
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524707B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes