HCID 178472229, compound → HCID 178432133, compound

HRID 869679Notes

Reaction equation

HRID 869679 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]([NH:17][C:18](=[O:25])[CH2:19][C:20](OCC)=[O:21])[NH:14][N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>N.CO>[CH3:1][C:2]1[C:3]([C:12]2[CH:16]=[C:15]3[N:17]=[C:18]([OH:25])[CH:19]=[C:20]([OH:21])[N:14]3[N:13]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 1

HCID 178472229HCID 178472229, compound

Product 1

HCID 178432133HCID 178432133, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

Method A (free form): A suspension of ethyl 3-{[3-(3-methylquinoxalin-2-yl)-1H-pyrazol-5-yl]amino}-3-oxopropanoate (20.0 g, 58.9 mmol) in 28% aqueous ammonia (295 mL) and methanol (1176 mL) was stirred overnight at room temperature, and then concentrated in vacuo. The residue was diluted with water (1500 mL) and ethyl acetate (1000 mL). The aqueous layer was concentrated in vacuo, and water (40 mL) was added. The mixture was acidified to pH 5-6 with 10% aqueous hydrochloric acid, and then ethanol (360 mL) was added. The resulting precipitate was collected and washed with 95% aqueous ethanol and ethanol to give 2-(3-methylquinoxalin-2-yl)pyrazolo[1,5-a]pyrimidine-5,7-diol. MS (ESI): m/z 292 (M−H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water (1500 mL) and ethyl acetate (1000 mL)
  3. concentrationThe aqueous layer was concentrated in vacuo, and water (40 mL)
  4. additionwas added
  5. additionethanol (360 mL) was added
  6. customThe resulting precipitate was collected
  7. washwashed with 95% aqueous ethanol and ethanol

Sources & evidence

ORD record
ord-4dace696853a40c39c2745f406ea492f
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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