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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
ノート
印刷プレビュー

反応式

HRID 1739938 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-86c46cd101eb42f6a0193efe1053d6cc
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05968937

反応ノート

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