Methyl 4-hydrazinobenzoate hydrochloride → Methyl 4-[4-(2-adamantylcarbamoyl)-5-cyclopentyl-pyrazol-1-yl]benzoate

HRID 1160548Notes

Reaction equation

Cl.[NH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[NH2:3].[CH:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH:15]1[NH:24][C:25](=[O:38])/[C:26](/[C:31]([CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=O)=[CH:27]\N(C)C)[CH2:21]2>C(O)C.C(O)(=O)C>[CH:16]12[CH2:17][CH:18]3[CH2:19][CH:20]([CH2:21][CH:14]([CH2:23]3)[CH:15]1[NH:24][C:25]([C:26]1[CH:27]=[N:3][N:2]([C:4]3[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=3)[C:31]=1[CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37]1)=[O:38])[CH2:22]2

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 4-hydrazinylbenzoate hydrochloride (Intermediate#123) (0.712 g, 3.51 mmol) was added in one portion to (Z)—N-(2-adamantyl)-2-(cyclopentanecarbonyl)-3-dimethylamino-prop-2-enamide (Intermediate#67), 1.21 g, 3.51 mmol) in ethanol (30 mL). 5 drops of acetic acid were added and the resulting solution was stirred at 80° C. for 2 hours and then cooled to ambient giving a precipitate. The reaction mixture was filtered and the product recovered, washed with ethanol (10 mL) and water (10 mL) before being dried under vacuum to give methyl 4-[4-(2-adamantylcarbamoyl)-5-cyclopentyl-pyrazol-1-yl]benzoate (0.620 g, 39.4%) as a white solid.

Workup

temperaturecooled
customto ambient giving a precipitate
filtrationThe reaction mixture was filtered
customthe product recovered
washwashed with ethanol (10 mL) and water (10 mL)
custombefore being dried under vacuum

Sources & evidence

ORD record: ord-72850da1804b408dbe61857dd4e54e7d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816391B2

Reaction notes

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