Diethyl Ether → Methyl 3-[5-amino-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate

HRID 1799394Notes

Reaction equation

[C:1]([C:3](=[CH:13]OCC)[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5])#[N:2].Cl.[NH:18]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])[NH2:19].CCN(C(C)C)C(C)C.CCOCC>C(O)C>[NH2:2][C:1]1[N:18]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])[N:19]=[CH:13][C:3]=1[C:4](=[O:5])[NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

2-cyano-N-cyclohexyl-3-ethoxy-prop-2-enamide (Intermediate #17) (605 mg, 2.73 mmol) and methyl 3-hydrazinylbenzoate hydrochloride (552 mg, 2.73 mmol) were suspended in ethanol (20 mL). DIPEA (352 mg, 2.73 mmol) was added and the mixture heated to 70° C. for 1 h. The reaction mixture was cooled to ambient and concentrated to a small volume. Water (50 mL) was added and the resulting solid recovered by filtration, redissolved in ethyl acetate (50 mL), dried (MgSO4) and evaporated to give a brown solid which was slurried with ether and recovered by filtration to give the title compound as light brown solid (443 mg, 47%).

Workup

temperatureThe reaction mixture was cooled to ambient and
concentrationconcentrated to a small volume
additionWater (50 mL) was added
filtrationthe resulting solid recovered by filtration
dissolutionredissolved in ethyl acetate (50 mL)
dry with materialdried (MgSO4)
customevaporated
customto give a brown solid which
filtrationrecovered by filtration

Sources & evidence

ORD record: ord-65af74981ce94f9aaf13a1f9821d0720
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344016B2

Reaction notes

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