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 1485429노트

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HRID 1485429 반응식
[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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 178460666HCID 178460666, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-626baeeebd6a4ee3b16942135ca96fff
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422292B2

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