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

反応式

HRID 3598 の反応式
[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

参加物

6

反応物 3

HCID 11905alpha-Bromo-o-chlorotoluene2 回HCID 24758Sodium hydrideHCID 70059534N-[4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin10(11H)-ylcarbonyl)phenyl]4-morpholineacetamide

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0377322d180742a7acad3e33e6f3f423
出典データセット
uspto-grants-1998_03
特許番号
US05733905

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