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

HRID 624751Notes

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

Participants

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

temperaturecooled to room temperature
custompartitioned between CH2Cl2 and H2O
customThe emulsion that formed between the layers
filtrationwas filtered off
washrinsed with H2O
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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