Ammonia → HCID 67252319, compound

HRID 2042093Notes

Reaction equation

HRID 2042093 reaction equation
Cl.C([O:4][C:5](=O)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([N:17]2[C:21]([NH2:22])=[CH:20][C:19]([C:23]([CH3:26])([CH3:25])[CH3:24])=[N:18]2)[CH:8]=1)C.[NH3:28].CO>>[NH2:22][C:21]1[N:17]([C:9]2[CH:8]=[C:7]([CH2:6][C:5]([NH2:28])=[O:4])[C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:18]=[C:19]([C:23]([CH3:26])([CH3:24])[CH3:25])[CH:20]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 67252199HCID 67252199, compound

Product 1

HCID 67252319HCID 67252319, compoundYield 41%

Procedure

[3-(5-amino-3-t-butyl-pyrazol-1-yl)naphthalen-1-yl]acetic acid ethyl ester hydrochloride (see WO 2006/071940, 1.60 g, 4.55 mmol) was treated with ammonia in methanol (7 M, 13 mL, 91 mmol) and the reaction mixture was heated in a sealed tube for 6 days. The solvent was removed in vacuo and the residue was chromatographed to provide 2-(3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)naphthalen-1-yl)acetamide (610 mg, 41% yield). MS (ESI) m/z: 323.3 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated in a sealed tube for 6 days
  2. customThe solvent was removed in vacuo
  3. customthe residue was chromatographed

Sources & evidence

ORD record
ord-4ae3159666e244d5b6b28e40a3abea30
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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