Water → N-(2-Amino-5-chloro-phenyl)-5-bromo-2-fluoro-benzamide

HRID 77079

반응식

HRID 77079 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[Cl:12][C:13]1[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>ClCCl.CN(C=O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][C:15]=1[NH:20][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:11]

참가 물질

7

반응물 4

HCID 962WaterHCID 72634-Chloro-1,2-diaminobenzeneHCID 27363155-Bromo-2-fluorobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 24699699N-(2-Amino-5-chloro-phenyl)-5-bromo-2-fluoro-benzamide수율 52%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

Method 7—Step a A mixture of 5-Bromo-2-fluoro-benzoic acid (3.00 g, 13.70 mmol), 4-chloro-benzene-1,2-diamine (2.42 g, 16.99 mmol), HATU (5.47 g, 14.38 mmol) and TEA (1.91 mL, 13.83 mmol) in dichloromethane (70 mL) and DMF (16 mL) was stirred at room temperature overnight, then water was added (80 mL) and left standing at room temperature overnight. The organic layer was divided and solvent removed under reduced pressure and the crude oil obtained was crystallized from the mixture of solvents dichloromethane:cyclohexane/3:1 (30 mL) to afford 2.19 g of the title compound (52%).

후처리

  1. waitleft
  2. waitstanding at room temperature overnight
  3. customsolvent removed under reduced pressure
  4. customthe crude oil obtained
  5. customwas crystallized from the mixture of solvents dichloromethane

출처 및 근거

ORD 기록
ord-b4ce010ef34c425eb8d782dbd571233d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835648B2

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