Water → N,N-Dimethyl-1H-indazole-3-carboxamide

HRID 1752585Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[N:2]1.C(C1NC=CN=1)([C:15]1[NH:16][CH:17]=CN=1)=O.Cl.CNC.O>CN(C)C=O>[CH3:15][N:16]([CH3:17])[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

1H-Indazole-3-carboxylic acid (5.0 g, 30.8 mmol) and carbonyl diimidazole (5.0 g, 33.9 mmol) were dissolved in N,N-dimethylformamide (150 mL) and heated to 60° C. After 2 hours, dimethylamine hydrochloride (4.0 g, 33.9) was added, and the reaction was stirred for an additional hour at 60° C. The reaction was poured into water, and the aqueous phase was extracted with ethyl acetate (3×150 mL). The combined organic phases were washed sequentially with aqueous sodium bicarbonate, 10% hydrochloric acid, water and brine. After drying over magnesium sulfate, filtering and concentrating in vacuo, the title compound was obtained.

Workup

extractionthe aqueous phase was extracted with ethyl acetate (3×150 mL)
washThe combined organic phases were washed sequentially with aqueous sodium bicarbonate, 10% hydrochloric acid, water and brine
dry with materialAfter drying over magnesium sulfate
filtrationfiltering
concentrationconcentrating in vacuo

Sources & evidence

ORD record: ord-be39450bb8c64f56b8274dc170259f00
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163007B2

Reaction notes

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