Ammonium Hydroxide → HCID 66959012, compound

HRID 1360494Notes

Reaction equation

HRID 1360494 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.[C:13]([O:17][C:18]([NH:20][C:21]([CH3:35])([CH3:34])[CH2:22][C:23]1[N:27]([CH2:28][CH2:29][CH3:30])[N:26]=[C:25]([C:31](O)=[O:32])[CH:24]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>CN(C=O)C.O>[NH2:3][C:31]([C:25]1[CH:24]=[C:23]([CH2:22][C:21]([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:35])[CH3:34])[N:27]([CH2:28][CH2:29][CH3:30])[N:26]=1)=[O:32]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66958795HCID 66958795, compound

Product 1

HCID 66959012HCID 66959012, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.68 g, 29.6 mmol) was added to a solution of 5-{2-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-1-propyl-1H-pyrazole-3-carboxylic acid (8.77 g, 27.0 mmol) and 1-hydroxybenzotriazole (4.00 g, 29.6 mmol) in DMF (44 mL) at ambient temperature. The mixture was stirred for 5.5 hours until a solution formed, then was cooled in an ice bath. Concentrated ammonium hydroxide (5.5 mL) was added and the cloudy solution was stirred for 10 minutes, then was allowed to warm to ambient temperature and stir overnight. Water (150 mL) was added and the mixture was extracted with chloroform (4×75 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was concentrated twice from xylene under reduced pressure to afford an oil that was purified on chromatography on a HORIZON HPFC system (silica gel, elution with ethyl acetate) to yield 8.21 g of tert-butyl 2-[3-(aminocarbonyl)-1-propyl-1H-pyrazol-5-yl]-1,1-dimethylethylcarbamate as a white solid.

Workup

  1. customformed
  2. temperaturewas cooled in an ice bath
  3. stirringthe cloudy solution was stirred for 10 minutes
  4. stirringstir overnight
  5. extractionthe mixture was extracted with chloroform (4×75 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. concentrationThe residue was concentrated twice from xylene under reduced pressure
  10. customto afford an oil that
  11. customwas purified on chromatography on a HORIZON HPFC system (silica gel, elution with ethyl acetate)

Sources & evidence

ORD record
ord-a4121fef388e4efa91dad82c91c81f9a
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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