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Hydrochloric Acid → 5-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid

HRID 624751
Notes
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Reaction equation

HRID 624751 reaction equation
C(OC([N:8]([CH:28]1[CH2:30][CH2:29]1)[C:9]1[N:14]2[N:15]=[CH:16][C:17]([CH:18]=[O:19])=[C:13]2[N:12]=[C:11]([C:20]2[S:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][CH:21]=2)[CH:10]=1)=O)(C)(C)C.Cl>O1CCOCC1>[CH:28]1([NH:8][C:9]2[N:14]3[N:15]=[CH:16][C:17]([CH:18]=[O:19])=[C:13]3[N:12]=[C:11]([C:20]3[S:24][C:23]([C:25]([OH:27])=[O:26])=[CH:22][CH:21]=3)[CH:10]=2)[CH2:29][CH2:30]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 583139645-(7-(Tert-butoxycarbonyl(cyclopropyl)amino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid

Product 1

HCID 583142305-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To 5-(7-(tert-butoxycarbonyl(cyclopropyl)amino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid (1 g, 2.33 mmol) was added 8 mL of 4M HCl in dioxane and another 5 mL of dioxane. The reaction mixture was stirred at 80° C. for 2 hours, cooled to room temperature and partitioned between CH2Cl2 and H2O. The emulsion that formed between the layers was filtered off and rinsed with H2O. The recovered solid was dried under vacuum to provide 627 mg of 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid as a red solid (82%). LCMS (M+1=329)

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between CH2Cl2 and H2O
  3. customThe emulsion that formed between the layers
  4. filtrationwas filtered off
  5. washrinsed with H2O
  6. customThe recovered solid was dried under vacuum

Sources & evidence

ORD record
ord-fd0c48a108ee4ab2b3fcdfb02689919b
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09303033B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes