Ammonium Hydroxide → 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide

HRID 549238Notes

Reaction equation

HRID 549238 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.[CH2:13]([N:16]1[C:20]([CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:19][C:18]([C:28]([OH:30])=O)=[N:17]1)[CH2:14][CH3:15].ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>CN(C)C=O.O>[CH2:13]([N:16]1[C:20]([CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:19][C:18]([C:28]([NH2:3])=[O:30])=[N:17]1)[CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671577251-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 671577891-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamideYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.06 g, 21.2 mmol) was added to a solution of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylic acid (4.88 g, 19.3 mmol) and 1-hydroxybenzotriazole (2.87 g, 21.2 mmol) in N,N-dimethylformamide (DMF) (24.4 mL) at room temperature. The mixture was stirred for two hours, cooled in an ice bath, and treated with concentrated ammonium hydroxide (3.9 mL). A precipitate formed, and the mixture was stirred 30 minutes at 0° C. Water (100 mL) was added, and the mixture was stirred for an additional ten minutes. The precipitate was isolated by filtration, washed with water, and dried on the vacuum filter funnel to provide 4.05 g of 1-propyl-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxamide as white crystals.

Workup

  1. temperaturecooled in an ice bath
  2. customA precipitate formed
  3. stirringthe mixture was stirred 30 minutes at 0° C
  4. stirringthe mixture was stirred for an additional ten minutes
  5. customThe precipitate was isolated by filtration
  6. washwashed with water
  7. customdried on the vacuum
  8. filtrationfilter funnel

Sources & evidence

ORD record
ord-6d08184d45bb454bab2f08f5333c89bf
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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