Ammonium Chloride → 2-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide

HRID 1667791노트

반응식

HRID 1667791 반응식
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:28]([O-:30])=[O:29])=[C:7]([NH:9][C:10]2[S:11][C:12]([C:25]([NH2:27])=[O:26])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:14]=2)[CH:8]=1)=O.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([CH2:1][C:3]2[CH:4]=[CH:5][C:6]([N+:28]([O-:30])=[O:29])=[C:7]([NH:9][C:10]3[S:11][C:12]([C:25]([NH2:27])=[O:26])=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:17][CH:16]=4)[N:14]=3)[CH:8]=2)[CH2:34][CH2:33]1

참가 물질

7

반응물 5

HCID 25517Ammonium ChlorideHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866428502-(5-Formyl-2-nitro-phenylamino)-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

생성물 1

HCID 866428512-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide수율 59.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 0.1041 g (0.239 mmole) of 2-(5-formyl-2-nitro-phenylamino)-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.47b), 5 mL of dichloromethane, 0.0781 g (0.772 mmole) of 1-methyl piperazine and 0.2665 (1.195 mmole) of sodium triacetoxyborohydride was stirred for 15 hours. The mixture was treated with 1 mL of saturated ammonium chloride, followed by 10 mL of saturated sodium bicarbonate and 5 mL of dichloromethane. The mixture was stirred for 45 minutes. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 1:99-20:80) to give 0.074 g of 2-[5-(4-methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide (VI.47c) as a light orange solid.

후처리

  1. stirringThe mixture was stirred for 45 minutes
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with methanol-dichloromethane (gradient 1:99-20:80)

출처 및 근거

ORD 기록
ord-993cc1a28a43476e880a4636852bc2b2
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044213B2

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