1-Hydroxybenzotriazole → HCID 178472752, compound

HRID 1093617Notes

Reaction equation

HRID 1093617 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:16]CN(C(C)C)C(C)C.[CH:25]1[CH:26]=[CH:27][C:28]2N(O)N=N[C:29]=2[CH:30]=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:48]([O:50][C:51](=[O:54])[CH2:52][NH2:53])[CH3:49]>CN(C=O)C.O>[CH2:48]([O:50][C:51](=[O:54])[CH2:52][NH:53][C:13]([C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:16][C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:30]=3)[CH:3]=2)[NH:12][N:11]=1)=[O:15])[CH3:49]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524124HCID 178524124, compound

Product 1

HCID 178472752HCID 178472752, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(3-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid (1 g, 0.00340 mol) in DMF (5 mL) was added DIPEA (1.976 g, 0.01529 mol), HOBt (0.574 g, 0.00425 mol) and EDCI.HCl (0.814 g, 0.00425 mol) at ambient temperature. After 5 minutes glycine ethyl ester hydrochloride (0.498 g, 0.00357 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and dried. The crude product was recrystallized from ethyl acetate to afford 0.54 g (36%) of {[5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid ethyl ester. LCMS: 380.15 (M+1)+, 92.05%. To a stirred solution of {[5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid ethyl ester (0.54 g, 0.00136 mmol) in a mixture of THF (50 mL), methanol (25 mL) and H2O (25 mL) was added LiOH.H2O (0.18 g, 0.0042 mol) at ambient temperature. The resulting mixture was stirred at ambient temperature overnight. Volatiles were removed by evaporation and the resulting residue was diluted with water, acidified with concentrated HCl solution. The resulting precipitate was isolated by filtration and dried afford 0.44 g (92%) of {[5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid. LCMS: 352.12 (M+1)+, 97.85%,

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customdried
  3. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f51f9898cdf64e20a0ad345590aff867
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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