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alpha-Bromo-o-chlorotoluene → N-[(2-Chlorophenyl)methyl]-N-[4-(5H-pyrrolo(2,1-c]-[1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl)-4-morpholineacetamide

HRID 3598
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HRID 3598 반응식
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:32])[CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.[CH:33]1[CH:38]=[C:37]([CH2:39]Br)[C:36]([Cl:41])=[CH:35][CH:34]=1.[H-].[Na+]>C(#N)C.O>[Cl:41][C:36]1[CH:35]=[CH:34][CH:33]=[CH:38][C:37]=1[CH2:39][N:23]([C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:16])=[CH:22][CH:21]=1)[C:24](=[O:32])[CH2:25][N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11905alpha-Bromo-o-chlorotoluene2회HCID 24758Sodium hydrideHCID 70059534N-[4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]4-morpholineacetamide

생성물 1

HCID 15340681N-[(2-Chlorophenyl)methyl]-N-[4-(5H-pyrrolo(2,1-c]-[1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl)-4-morpholineacetamide수율 126.9%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6342Acetonitrile용매

실험 절차

A mixture of 0.11 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-4-morpholineacetamide, 56 mg of O-chlorobenzyl bromide and 0.41 g of K2 CO3 in 5 ml of acetonitrile is heated at reflux for 18 hours. An additional 30 mg of O-chlorobenzyl bromide and 0.4 mmol of sodium hydride is added followed by heating for 24 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried with Na2SO4 and evaporated to give 0.18 g of a residue which is purified by chromatography on silica gel with 1:1 ethyl acetate-methylene chloride to give 80 mg of off white solid. MS(CI): 555 (M+H).

후처리

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. temperatureby heating for 24 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried with Na2SO4
  6. customevaporated

출처 및 근거

ORD 기록
ord-0377322d180742a7acad3e33e6f3f423
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05733905

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