Cyclopropanecarbonyl chloride → N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide

HRID 2036929Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]2[N:3]=1.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.CCN(C(C)C)C(C)C>O1CCCC1>[CH:9]1([NH:8][C:6]2[N:5]3[N:12]=[CH:13][C:14]([CH:15]=[O:16])=[C:4]3[N:3]=[C:2]([NH:1][C:20]([CH:17]3[CH2:19][CH2:18]3)=[O:21])[CH:7]=2)[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

To 5-amino-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (step b) (58 mg, 0.266 mmol) in 1.0 mL tetrahydrofuran was added cyclopropane carbonyl chloride (38 ul, 0.419 mmol) and DIPEA (39.0 ul). The reaction mixture was heated at 60° C. for one hour. The reaction was partitioned between ethyl acetate and water, the organic layer was dried under sodium sulfate concentrated on high vac to yield N-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide. The crude product was taken to next step without further purification. LCMS (M+1=286)

Workup

customThe reaction was partitioned between ethyl acetate and water
customthe organic layer was dried under sodium sulfate
concentrationconcentrated on high vac

Sources & evidence

ORD record: ord-7fc34ce7c2984d26aff3b70ebfb5d726
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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