Hydrochloric Acid → 6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 216498노트

반응식

HRID 216498 반응식
CO[C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:8]2[N:9]=CNC=2[CH:6]=1)=[O:4].[CH3:24][O:25]C(C1C(NC2C=CC(Br)=CC=2)=C(Cl)C2N=CNC=2C=1)=O.C1C(=O)[N:50](Cl)C(=O)C1.Cl.[C:55](=[O:58])(O)[O-].[Na+].OS([O-])=O.[Na+].[CH3:65][N:66]([CH:68]=O)[CH3:67]>O>[OH:25][CH2:24][CH2:55][O:58][NH:50][C:3]([C:5]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:8]2[N:9]=[CH:68][N:66]([CH3:65])[C:67]=2[CH:6]=1)=[O:4]

참가 물질

9

반응물 7

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 31398Chlorosuccinimide2회HCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 668983426-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl esterHCID 688177756-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester

생성물 1

HCID 588906256-(4-Bromo-2-chloro-phenylamino)-7-chloro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide수율 57%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

6-(4-Bromo-2-chloro-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester 10dd: 6-(4-Bromo-phenylamino)-7-chloro-3H-benzoimidazole-5-carboxylic acid methyl ester 8g (0.225 g, 0.591 mmol) is dissolved in DMF (2 mL) and NCS (79 mg, 0.591 mmol) is added. After the NCS is in solution concentrated HCl (0.005 mL, 0.059 mmol) is added. After 2 hours, sodium bicarbonate, water and NaHSO3 are added to the reaction mixture. Solids are filtered and washed with water and ether to give 0.141 g (57%) of clean desired product as a tan solid. MS APCI (−) m/z 414, 416 (M−, Br pattern) detected.

후처리

  1. additionis added
  2. filtrationSolids are filtered
  3. washwashed with water and ether

출처 및 근거

ORD 기록
ord-02c8520c1cdf421da695ec3b668d0d92
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193229B2

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