Triethylamine → HCID 68622096, compound

HRID 407161Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:19](O)=[O:20])=[N:15][NH:16]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.CN.C1C=CC2N(O)N=[N:31][C:29]=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:29][NH:31][C:19]([C:14]1[C:13]2[C:17](=[CH:18][C:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[CH:11][CH:12]=2)[NH:16][N:15]=1)=[O:20]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 6-(4-nitrophenyl)-1H-indazole-3-carboxylic acid (140 mg, 0.5 mmol), methyl amine hydrochloride (45 mg, 0.6 mmol), HOBt (80 mg, 0.6 mmol), and triethylamine (0.3 Ml, 2 mmol) in N,N-dimethylformamide (5 Ml), was added EDCI (142 mg, 0.7 mmol). After the mixture was stirred at 70° C. for 12 h, the mixture was cooled to room temperature, and ethyl acetate and saturated sodium bicarbonate solution were added. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give N-methyl-6-(4-nitrophenyl)-1H-indazole-3-carboxamide (70 mg).

Workup

temperaturethe mixture was cooled to room temperature
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialthe combined organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a1bbeebb73444b27aabce70172a6f8f6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754209B2

Reaction notes

Loading…