Water → HCID 10133732, compound

HRID 1374725Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]([C:19](=O)[CH:20]=[CH:21]N(C)C)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH:26]1([NH:29][C:30]([NH2:32])=[NH:31])[CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:26]1([NH:29][C:30]2[N:32]=[C:19]([C:18]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9][N:10]4[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:11]=34)[CH:20]=[CH:21][N:31]=2)[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(4-fluorophenyl)-3-(3-(dimethylamino)-2-propenoyl)-6-cyanopyrazolo[1,5-a]pyridine (1.3 g, 3.9 mmol) in dimethylformamide (20 mL), under N2, was added N-cyclopropylguanidine (0.78 g, 7.8 mmol) and potassium carbonate (1.1 g, 7.8 mmol). The mixture was stirred and heated at 100° C. for 17 h and then additional N-cyclopropyl-guanidine (0.39 g, 3.9 mmol) and potassium carbonate (0.55 g, 3.9 mmol) were added. The mixture was heated at 100° C. for an additional 4 h and then the reaction mixture was cooled and water added. The resulting solid was collected by filtration. This solid was dissolved in diethyl ether and purified using chromatography to give the title compound as a yellow solid, 0.39 g (28%). 1H NMR (d6-DMSO) δ 0.50 (m, 2H), 0.69 (d, 2H, J=4.0 Hz), 2.69 (m, 1H), 6.29 (d, 1H, J=8.0 Hz), 7.34 (t, 2H, J=8.0 Hz), 7.47 (d, 1H, J=4.0 Hz), 7.69 (m, 3H), 8.11 (d, 1H, J=4.0 Hz), 8.56 (br 5,1H) MS (ES+) m/z 370 (M++H).

Workup

temperatureThe mixture was heated at 100° C. for an additional 4 h
temperaturethe reaction mixture was cooled
filtrationThe resulting solid was collected by filtration
dissolutionThis solid was dissolved in diethyl ether
custompurified

Sources & evidence

ORD record: ord-c24013ce8045461b8c0fee28bd83676c
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166597B2

Reaction notes

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