Diisopropylethylamine → 2-(2-trifluoromethylphenylamino)-benzooxazole-5-carboxylic acid (1H-indazol-6-yl)-amide

HRID 388983

Reaction equation

HRID 388983 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[OH:20])[C:5]([NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[N:13][NH:14]2)=[CH:10][CH:9]=1)=[O:6].[N:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([F:33])([F:32])[F:31])=[C:22]=S.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([NH:7][C:5]([C:4]3[CH:17]=[CH:18][C:19]4[O:20][C:22]([NH:21][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:31])([F:32])[F:33])=[N:1][C:2]=4[CH:3]=3)=[O:6])[CH:16]=2)[CH:12]=[N:13]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 7371622-(Trifluoromethyl)phenyl isothiocyanateHCID 684449953-amino-4-hydroxy-N-(1H-indazol-6-yl)-benzamide

Product 1

HCID 595225792-(2-trifluoromethylphenylamino)-benzooxazole-5-carboxylic acid (1H-indazol-6-yl)-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the aminophenol (0.5 mmol) from above in DMF (2 mL) was added with 1-isothiocyanato-2-trifluoromethylbenzene (0.6 mmol) and DIEA (1 mmol). The reaction mixture was subjected to microwave irradiation at 120° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with water (20 mL). The solid formed was collected by filtration, washed with water, and dried in vacuo. The crude product was purified on a silica gel column chromatography using MeOH/DCM as eluent to provide 2-(2-trifluoromethylphenylamino)-benzooxazole-5-carboxylic acid (1H-indazol-6-yl)-amide, obtained as a yellow solid. MS: m/z 438 (M+H)+.

Workup

  1. customirradiation at 120° C. for 1 h
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customThe crude product was purified on a silica gel column chromatography

Sources & evidence

ORD record
ord-c7c76c0bbd7742dc8815e12b6a9e9f72
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Linked notes

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