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Sodium Hydroxide → N-[4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-yl)carbonyl]3-chlorophenyl]3-fluoro-2-methylbenzamide

HRID 1739938
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HRID 1739938 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9]2)=[O:7])=[C:4]([Cl:24])[CH:3]=1.[F:25][C:26]1[C:27]([CH3:35])=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30].C1(CS(NC2C=CC(C(N3C4C=CC=CC=4CN4C=CC=C4C3)=O)=CC=2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>ClCCl.C(N(CC)CC)C>[CH:18]1[C:13]2[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9][N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][CH:34]=[C:26]([F:25])[C:27]=4[CH3:35])=[CH:3][C:4]=3[Cl:24])=[O:7])[C:14]=2[CH:15]=[CH:16][CH:17]=1
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참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 27792403-Fluoro-2-methylbenzoyl chlorideHCID 2183697910-[4-[[(Phenylmethyl)sulfonyl]amino]benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepineHCID 218369946,7-Dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepin

생성물 1

HCID 21837130N-[4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-yl)carbonyl]3-chlorophenyl]3-fluoro-2-methylbenzamide
수율 106.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo-[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.08 g of 3-fluoro-2-methylbenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred for 2 hours at room temperature and then 2 ml of 1 NaOH added. The volatiles are evaporated under vacuum and the residue dissolved in 2 ml of tetrahydrofuran and 1 ml of methanol. The mixture is stirred for 2 hours and evaporated and the residue diluted with 2 ml of 1 N NaOH and 5 ml of water. The mixture is extracted with ethyl acetate (15 ml) and the extract washed with brine and dried (Na2SO4). The solvent is removed and the residue triturated with diethyl ether-hexane to give 0.15 g of white solid: Mass Spectrum (CI)474(M+H, Cl35); 476(M+H, Cl37).

후처리

  1. customThe volatiles are evaporated under vacuum
  2. dissolutionthe residue dissolved in 2 ml of tetrahydrofuran
  3. stirringThe mixture is stirred for 2 hours
  4. customevaporated
  5. additionthe residue diluted with 2 ml of 1 N NaOH and 5 ml of water
  6. extractionThe mixture is extracted with ethyl acetate (15 ml)
  7. washthe extract washed with brine
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed
  10. customthe residue triturated with diethyl ether-hexane

출처 및 근거

ORD 기록
ord-86c46cd101eb42f6a0193efe1053d6cc
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05968937

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