Ammonia → 3-[4-(2-Chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid amide

HRID 929782Notes

Reaction equation

HRID 929782 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:20]([Cl:25])=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:13][CH:12]=2)[CH:7]=1)=O)C.[NH3:26]>CCO>[Cl:25][C:20]1[C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:7]=[C:6]([C:4]([NH2:26])=[O:3])[O:10][N:9]=3)=[CH:12][CH:13]=2)=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 902025533-[4-(2-Chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid ethyl ester2×

Product 1

HCID 762846283-[4-(2-Chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid amideYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[4-(2-Chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid ethyl ester (which may be prepared as described in Preparation of Intermediate 11; 57 mg, 0.16 mmol) was taken up in 2M NH3 in EtOH. The mixture was stirred overnight, transferred to a 20 mL scintillation vial and evaporated after several hours at room temperature. The residue was purified twice by chromatography, eluting first with 35-80% EtOAc/hexanes and then with 50-90% EtOAc/hexanes to give 3-[4-(2-chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid amide (7.2 mg, 14%). HRMS Calcd. for C16H13ClN3O3 (M+H)+, 330.0640. Found: 330.0637.

Workup

  1. customevaporated after several hours at room temperature
  2. customThe residue was purified twice by chromatography
  3. washeluting first with 35-80% EtOAc/hexanes

Sources & evidence

ORD record
ord-cbdfd19d38d649a69f1e25f6d16944b7
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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