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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Acetic Acid → (1S,2R)-5'-(4-chlorophenyl)-2-(methoxymethyl)-6',7'-dimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

HRID 1772333
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HRID 1772333 반응식
[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([CH3:16])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=O.C1(C(=[N:31][C@@:32]2([C:38](OCC)=[O:39])[CH2:34][C@H:33]2[CH2:35][O:36][CH3:37])C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].C(O)(=O)C>C1COCC1.C(O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[C:6]3[C:5]([CH3:16])=[C:4]([CH3:17])[S:3][C:2]=3[NH:1][C:38](=[O:39])[C@@:32]3([CH2:34][C@H:33]3[CH2:35][O:36][CH3:37])[N:31]=2)=[CH:10][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 719710(2-Amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanoneHCID 23665647Potassium tert-butoxideHCID 86706920(1S,2R)-ethyl 1-((diphenylmethylene)amino)-2-(methoxymethyl)cyclopropanecarboxylate

생성물 1

HCID 136338064(1S,2R)-5'-(4-chlorophenyl)-2-(methoxymethyl)-6',7'-dimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (7.09 g, 26.7 mmol) and (1S,2R)-ethyl 1-((diphenylmethylene)amino)-2-(methoxymethyl)cyclopropanecarboxylate (6 g, 17.78 mmol) in anhydrous THF (100 mL) was slowly (over 5 min) added a solution of potassium tert-butoxide (1 M in THF) at rt. The reaction was heated to 60° C. for approximately 20 h before acetic acid (10.68 g, 178 mmol) and absolute ethanol (20 mL) were added at 60° C. THF was distilled off, and the reaction was heated to reflux for 3 h. The reaction was cooled to rt before silica gel was added, and the solvent was removed under vacuum. The dry silica gel was packed and the product was purified by flash chromatography (EtOAc/hexane 1:19 to 6:14) to give (1S,2R)-5′-(4-chlorophenyl)-2-(methoxymethyl)-6′,7′-dimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one a solid (3.7 g). LRMS (M+H)+: 375 m/z.

후처리

  1. custom(over 5 min)
  2. additionwere added at 60° C
  3. distillationTHF was distilled off
  4. temperaturethe reaction was heated
  5. temperatureto reflux for 3 h
  6. additionwas added
  7. customthe solvent was removed under vacuum
  8. customthe product was purified by flash chromatography (EtOAc/hexane 1:19 to 6:14)

출처 및 근거

ORD 기록
ord-42b200e45a4d42a6bf1ac9e82aa1c07c
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249161B2

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