1-Methylpiperazine → 2-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester

HRID 1667679

반응식

HRID 1667679 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:13]=2[N+:20]([O-:22])=[O:21])=[N:8][C:7]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:5])[CH3:2].[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH2:18][N:33]3[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]3)[CH:15]=[CH:14][C:13]=2[N+:20]([O-:22])=[O:21])=[N:8][C:7]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866428052-(5-Formyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester

생성물 1

HCID 866428062-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester수율 68.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 0.080 g (0.2 mmole) of 2-(5-formyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VI.1b), 2 mL of dichloromethane and 0.027 mL (0.24 mmole) of 1-methyl-piperizine was stirred at ambient temperature for 10 minutes, then 0.064 g (0.3 mmole) of sodium triacetoxyborohydride was added. The mixture was stirred at ambient temperature for 2 hours and was then diluted with 10 mL of dichloromethane. The mixture was washed with 3 mL of saturated sodium bicarbonate. The aqueous layer was extracted twice with 5 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 0:100-5:95) to give 0.066 g of 2-[5-(4-methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VI.1c) as an orange solid.

후처리

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. washThe mixture was washed with 3 mL of saturated sodium bicarbonate
  3. extractionThe aqueous layer was extracted twice with 5 mL of dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with methanol-dichloromethane (gradient 0:100-5:95)

출처 및 근거

ORD 기록
ord-78bbc88d7e6e4d47bf008a03242d9aca
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044213B2

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