Ethanol → N-(cyclopropylmethyl)-5-(3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide

HRID 383702Notes

Reaction equation

[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][N:16]4[N:19]=[CH:20][C:21]([CH:22]=O)=[C:15]4[N:14]=3)=[CH:11][CH:12]=2)=[O:7])[CH2:3][CH2:2]1.C(O)C.[NH:27]1[CH2:33][C:31](=[O:32])[NH:30][C:28]1=[O:29].N1CCCCC1>O>[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][N:16]4[N:19]=[CH:20][C:21]([CH:22]=[C:33]5[C:31](=[O:32])[NH:30][C:28](=[O:29])[NH:27]5)=[C:15]4[N:14]=3)=[CH:11][CH:12]=2)=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To the reaction flask, N-(cyclopropylmethyl)-5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide (10 mg, 0.030 mmol) was added to ethanol (0.5 mL) along with hydantoin (3 mg, 0.03 mmol) and piperidine (3 uL, 0.03 mmol). The reaction was heated at 80° C. for 1 hour in the microwave then cooled to room temperature and diluted with water. The solid was collected by filtration, washed with water, 50% ethanol/water, and then 100% ethanol. The material was dried under vacuum overnight. The product, N-(cyclopropylmethyl)-5-(3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide, was recovered as a solid in 29% yield. LCMS (M+1=409)

Workup

temperaturethen cooled to room temperature
filtrationThe solid was collected by filtration
washwashed with water, 50% ethanol/water
customThe material was dried under vacuum overnight
customThe product, N-(cyclopropylmethyl)-5-(3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide, was recovered as a solid in 29% yield

Sources & evidence

ORD record: ord-7a0f892f27b04e85ad4c699247afb75f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367681B2

Reaction notes

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