Dimethylformamide → 1,3-Dimethyl-1H-pyrazole-5-carboxylic acid

HRID 1668577Notes

Reaction equation

HRID 1668577 reaction equation
[NH2:1][C:2]1[C:19]([OH:20])=[CH:18][C:5]2[CH2:6][CH2:7][N:8](C(OC(C)(C)C)=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH3:21][N:22]1[C:26]([C:27](Cl)=[O:28])=[CH:25][C:24]([CH3:30])=[N:23]1.CN(C)C=O>ClCCl>[CH3:21][N:22]1[C:26]([C:27]2[O:20][C:19]3[C:2]([N:1]=2)=[CH:3][C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=2[CH:18]=3)=[CH:25][C:24]([CH3:30])=[N:23]1.[CH3:21][N:22]1[C:26]([C:27]([OH:12])=[O:28])=[CH:25][C:24]([CH3:30])=[N:23]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 591504721,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 2

HCID 5877211,3-Dimethyl-1H-pyrazole-5-carboxylic acidHCID 59150521HCID 59150521, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Procedure 2 from 1,1-dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate and 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride. The latter reactant had been obtained in dichloromethane solution from the reaction of 1,3-dimethyl-1H-pyrazole-5-carboxylic acid (1.3 eq.) in the presence of a catalytic quantity of dimethylformamide, followed by evaporation of the volatiles after 1.5 h at 25° C.

Sources & evidence

ORD record
ord-ac0b087de61c47e38806b6dbec05fce1
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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