Diisopropylethylamine → Methyl 4-[5-amino-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate

HRID 1799391Notes

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:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)[NH2:19].CCN(C(C)C)C(C)C>C(O)C>[NH2:2][C:1]1[N:18]([C:20]2[CH:21]=[CH:22][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][CH:29]=2)[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 4-hydrazinylbenzoate hydrochloride (Intermediate #123) (552 mg, 2.73 mmol) were suspended in ethanol (20 mL). DIPEA (351 mg, 2.73 mmol) was added and the mixture heated to 70° C. for 1 h. The reaction mixture was cooled to ambient and the resulting precipitate recovered by filtration, washed with ether and dried in vacuo to give the title compound as a white solid. (618 mg 66%)

Workup

temperatureThe reaction mixture was cooled to ambient and the resulting precipitate
filtrationrecovered by filtration
washwashed with ether
customdried in vacuo

Sources & evidence

ORD record: ord-274d05aa25e34cdab743830b6d2148ca
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344016B2

Reaction notes

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