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

HRID 1163428Notes

Reaction equation

HRID 1163428 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-7d55df53496045ce8b4c2b986b516a30
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

Loading…