Water → 4-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206136Notes

Reaction equation

HRID 2206136 reaction equation
[C:1]([N:5]1[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:14][CH3:15])[C:8]=2[C:7]([C:16]2[CH:17]=[C:18]([C:21]([OH:23])=O)[S:19][CH:20]=2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CC[N:26]=C=NCCCN(C)C.Cl.O>CN(C=O)C>[C:1]([N:5]1[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:14][CH3:15])[C:8]=2[C:7]([C:16]2[CH:17]=[C:18]([C:21]([NH2:26])=[O:23])[S:19][CH:20]=2)=[N:6]1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1179879274-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acid

Product 1

HCID 1179876894-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamideYield 19,518.301%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acid (1.50 g) in DMF (200 mL) were added EDCI hydrochloride (4.34 mg) and HOBt ammonium salt (3.44 g) at room temperature, and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added water at 0° C., and the white precipitate was collected by filtration. The obtained white solid was washed with water and saturated aqueous sodium hydrogencarbonate solution, and dried in vacuum to give the title compound (1.46 g).

Workup

  1. filtrationthe white precipitate was collected by filtration
  2. washThe obtained white solid was washed with water and saturated aqueous sodium hydrogencarbonate solution
  3. customdried in vacuum

Sources & evidence

ORD record
ord-32506cc08c054890abf855693b5e7b86
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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