Hydrochloric Acid → 5-(3-Carbamoyl-phenyl)-oxazole-4-carboxylic acid [1-(5-acetyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-amide

HRID 2065310Notes

Reaction equation

HRID 2065310 reaction equation
[C:1]([C:4]1[O:8][C:7]([CH2:9][N:10]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[N:19]=[CH:20][O:21][C:22]=3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=3)=[O:17])[CH:12]=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH4+].[OH-:32].Cl>S(=O)(=O)(O)O>[C:1]([C:4]1[O:8][C:7]([CH2:9][N:10]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[N:19]=[CH:20][O:21][C:22]=3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29](=[O:32])[NH2:30])[CH:24]=3)=[O:17])[CH:12]=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 669289435-(3-Cyano-phenyl)-oxazole-4-carboxylic acid [1-(5-acetyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-amide

Product 1

HCID 669286515-(3-Carbamoyl-phenyl)-oxazole-4-carboxylic acid [1-(5-acetyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-(3-Cyano-phenyl)-oxazole-4-carboxylic acid [1-(5-acetyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-amide (50 mg, 0.112 mmol) in 97% sulfuric acid (0.17 mL) was stirred at rt overnight. The reaction mixture was then poured onto crushed ice, adjusted to pH 9 with NH4OH, and then strongly acidified with HCl 25%. The precipitate was filtered and washed with water until neutral pH. After drying, the title compound was obtained as a beige solid. LC-MS-conditions 02: tR=0.81 min; [M+H]+=420.12.

Workup

  1. additionThe reaction mixture was then poured
  2. customonto crushed ice
  3. filtrationThe precipitate was filtered
  4. washwashed with water until neutral pH
  5. customAfter drying

Sources & evidence

ORD record
ord-1c9b4c50121249889c7cea8444fcfef1
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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