Acetic Acid → 2-amino-6-fluoro-N-(2-methyl-1-phenyl-1H-imidazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1850695Notes

Reaction equation

[NH2:1][C:2]1[C:6]([C:7]([NH:9][C:10]2[N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:15])=[N:13][CH:14]=2)=[O:8])=[C:5]([NH2:22])[NH:4][N:3]=1.C(N(C(C)C)[CH:27]=[C:28]([F:31])[CH:29]=O)(C)C.C(O)(=O)C>C(O)(C)C.O>[NH2:22][C:5]1[C:6]([C:7]([NH:9][C:10]2[N:11]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:12]([CH3:15])=[N:13][CH:14]=2)=[O:8])=[C:2]2[N:1]=[CH:27][C:28]([F:31])=[CH:29][N:3]2[N:4]=1

Participants

Conditions

Temperature: 88 °C

Procedure

To a mixture of 3,5-diamino-N-(2-methyl-3-phenyl-imidazol-4-yl)-1H-pyrazole-4-carboxamide (116 mg, 0.3902 mmol), 3-(diisopropylamino)-2-fluoro-prop-2-enal (67.59 mg, 0.3902 mmol) in isopropanol (0.58 mL) and water (0.58 mL) was added acetic acid (0.221 mL, 3.904 mmol) and the solution was heated to 88° C. for 2.5 h. The reaction mixture was partitioned between EtOAc and saturated sodium carbonate solution. Combined organic extract was dried (MgSO4), and concentrated in vacuo to give as a redish oil that was purified by fractionlynx. Clean fractions were freeze-dried to give 2-amino-6-fluoro-N-(2-methyl-1-phenyl-1H-imidazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as a yellow solid. (16.4 mg, 8.5%). MS (ES+) 352.2.

Workup

customThe reaction mixture was partitioned between EtOAc and saturated sodium carbonate solution
extractionCombined organic extract
dry with materialwas dried (MgSO4)
concentrationconcentrated in vacuo
customto give as a redish oil that
customwas purified by fractionlynx
customClean fractions were freeze-dried

Sources & evidence

ORD record: ord-33fcb509d290472b87323b7b99d83a75
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957078B2

Reaction notes

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