1,1'-Carbonyldiimidazole → N-cyclopropyl-4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzamide

HRID 1255870Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[N:11]([N:13]=[CH:14][C:15]=3[C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=3)[CH:12]=2)[CH:4]=[N:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.C1C=C[C:40]2N(O)N=[N:43][C:41]=2[CH:42]=1.C1(N)CC1>CN(C=O)C>[CH:41]1([NH:43][C:20](=[O:22])[C:19]2[CH:23]=[CH:24][C:16]([C:15]3[CH:14]=[N:13][N:11]4[CH:12]=[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)[CH:8]=[N:9][C:10]=34)=[CH:17][CH:18]=2)[CH2:42][CH2:40]1

Participants

Conditions

Temperature: 120 °C

Procedure

4-[6-(1-Methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzoic acid (50 mg, 0.16 mmol) was dissolved in DMF (2 mL). Resin bound CDI (288 mg, 0.4 mmol), HOBT (26 mg, 0.17 mmol), and cyclopropylamine (20 mg, 0.32 mmol) was added. The reaction was sealed and heated in the microwave at 120° C. for 20 minutes. The reaction was cooled to ambient temperature, filtered and purified by reverse phase chromatography to give N-cyclopropyl-4-[6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]benzamide as a yellow solid: LC/MS [M+H]=359.0.

Workup

additionwas added
customThe reaction was sealed
temperatureThe reaction was cooled to ambient temperature
filtrationfiltered
custompurified by reverse phase chromatography

Sources & evidence

ORD record: ord-12e3b6ad07d540a78e85673b3ad3029c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461162B2

Reaction notes

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