Dimethylformamide → HCID 178472751, compound

HRID 1093599Notes

Reaction equation

HRID 1093599 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN([CH:21]([CH3:23])C)C(C)C.C1C=CC2N([OH:33])N=NC=2C=1.CCN=C=NCCC[N:42]([CH3:44])C.Cl.CN([CH:49]=[O:50])C>O>[CH2:21]([O:33][C:49](=[O:50])[CH2:44][NH:42][C:12]([C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:11][N:10]=1)=[O:14])[CH3:23]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524117HCID 178524117, compound

Product 1

HCID 178472751HCID 178472751, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid (1.25 g, 0.00665 mol) in DMF (3 mL) was added DIPEA (4.296 g 0.03324 mol), HOBt (1.123 g, 0.00831 mol) and EDCI.HCl (1.593 g, 0.00831 mol) at ambient temperature. After 2 minutes glycine acid ethyl ester hydrochloride (0.928 g, 0.00665 mol) was and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was collected and washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 0.76 g (42% of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid ethyl ester. LCMS: 274.11 (M+1)+, 96.7%. To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid ethyl ester (0.615 g, 0.0025 mol) in a mixture of THF (10 mL), methanol (5 mL) and H2O (5 mL) was added LiOH.H2O (0.283 g, 0.00675 mol) at ambient temperature. The reaction mixture was stirred at the same temperature for 2 hours. Volatiles were evaporated and the residue was diluted with water, acidified with 10% HCl solution. The resulting precipitate was isolated by filtration, washed water followed by hexane and to afford 0.238 g (38%) of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid. LCMS: 246.08 (M+1)+, 95.60%

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. customThe ethyl acetate layer was collected
  3. washwashed with brine solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c98b832190440d2a578008ffbaaf360
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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