Cyclopropylamine → (N-cyclopropyl)-6,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxamide

HRID 1243823Notes

Reaction equation

[C:1]1([C:7]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][C:14]3[NH:13][N:12]=[C:11]([C:16]([OH:18])=O)[C:10]=3[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:25]1([NH2:28])[CH2:27][CH2:26]1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1>ClCCl>[CH:25]1([NH:28][C:16]([C:11]2[C:10]3[CH:9]=[CH:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:15][C:14]=3[NH:13][N:12]=2)=[O:18])[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 20 °C

Procedure

Starting with a mixture of 1.23 g of 6,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxylic acid, 0.26 cm3 of cyclopropylamine, 0.86 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 60 mg of hydroxybenzotriazole in solution in 30 cm3 of dichloromethane, and after stirring for 18 hours at a temperature in the region of 20° C., washing with twice 30 cm3 of distilled water and purifying the crude product obtained by flash chromatography on silica gel (30–70 μm), eluting with a cyclohexane/ethyl acetate (60/40) mixture, 0.58 g of (N-cyclopropyl)-6,6-diphenyl-6,7-dihydro-1H-indazole-3-carboxamide is obtained in the form of a yellow solid, the characteristics of which are as follows:

Workup

washwashing with twice 30 cm3 of distilled water
custompurifying the crude product
customobtained by flash chromatography on silica gel (30–70 μm)
washeluting with a cyclohexane/ethyl acetate (60/40) mixture

Sources & evidence

ORD record: ord-677c95aaa1d742788d93011560fa819f
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119115B2

Reaction notes

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