Water → 4-{[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-amino}-3-nitro-benzoic acid methyl ester

HRID 18580

Reaction equation

HRID 18580 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[Cl:15][C:16]1[S:20][C:19]([C:21]2[O:25][N:24]=[C:23]([CH2:26][NH2:27])[CH:22]=2)=[CH:18][CH:17]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:27][CH2:26][C:23]2[CH:22]=[C:21]([C:19]3[S:20][C:16]([Cl:15])=[CH:17][CH:18]=3)[O:25][N:24]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoateHCID 68616593(5-(5-Chlorothiophen-2-yl)isoxazol-3-yl)methanamine

Product 1

HCID 686158574-{[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-amino}-3-nitro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 634.4 mg (3.19 mmol) 4-Fluoro-3-nitro-benzoic acid methyl ester in 12 mL DMF were added 800.0 mg (3.19 mmol) C-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-methylamine and 0.88 mL (6.37 mmol) triethylamine. The reaction mixture was stirred at room temperature for 16 h. 12 mL water was added. The precipitate was filtered off and washed with water. The yellow crystalline material was dried under reduced pressure at 40° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customThe yellow crystalline material was dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-d15e672edb1b49a3871841e558853d66
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

Loading…