Ethyl 1-((2-amino-5-bromophenylamino)methyl)cyclopropanecarboxylate → 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropan]-2(1H)-one

HRID 1485429ノート

反応式

HRID 1485429 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1([C:14]([O:16]CC)=O)[CH2:13][CH2:12]1>C1(C)C=CC=CC=1.O.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:14](=[O:16])[C:11]3([CH2:10][NH:9][C:3]=2[CH:4]=1)[CH2:13][CH2:12]3

参加物

5

反応物 1

HCID 86718502Ethyl 1-((2-amino-5-bromophenylamino)methyl)cyclopropanecarboxylate

生成物 1

HCID 709789007-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropan]-2(1H)-one収率 75%

試薬・触媒・溶媒 3

HCID 178460666HCID 178460666、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of ethyl 1-((2-amino-5-bromophenylamino)methyl)cyclopropanecarboxylate (624 mg, 2.0 mmol) in toluene (15 mL) was added dropwise tetraisopropoxytitanium (1.2 g, 4.0 mmol). After addition was complete, the reaction was stirred for 12 hours at 90° C. The mixture was diluted with water (200 mL), extracted with ethyl acetate (200 mL). The organic layer was separated, dried by sodium sulfate, filtered and concentrated to give the crude 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropan]-2(1H)-one (400 mg, 75%) as white solid, used for the next step without further purification.

後処理

  1. additionAfter addition
  2. extractionextracted with ethyl acetate (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried by sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-626baeeebd6a4ee3b16942135ca96fff
出典データセット
uspto-grants-2016_08
特許番号
US09422292B2

反応ノート

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