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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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3-Hydroxyazetidine hydrochloride → 5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({2-[(3-hydroxyazetidin-1-yl)carbonyl]imidazo[1,2-b]pyridazin-6-yl}amino)thiophene-3-carboxamide

HRID 1799587
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HRID 1799587 반응식
[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:11][C:10]=2[F:20])[S:6][C:5]=1[NH:21][C:22]1[CH:23]=[CH:24][C:25]2[N:26]([CH:28]=[C:29]([C:31](OCC)=[O:32])[N:30]=2)[N:27]=1)=[O:3].C[Al](C)C.Cl.[OH:41][CH:42]1[CH2:45][NH:44][CH2:43]1>O1CCCC1>[F:15][C:14]1[CH:13]=[C:12]([C:16]([OH:19])([CH3:18])[CH3:17])[CH:11]=[C:10]([F:20])[C:9]=1[C:7]1[S:6][C:5]([NH:21][C:22]2[CH:23]=[CH:24][C:25]3[N:26]([CH:28]=[C:29]([C:31]([N:44]4[CH2:45][CH:42]([OH:41])[CH2:43]4)=[O:32])[N:30]=3)[N:27]=2)=[C:4]([C:2]([NH2:1])=[O:3])[CH:8]=1
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참가 물질

5

반응물 3

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 16682925TrimethylaluminumHCID 58216619Ethyl 6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)imidazo[1,2-b]pyridazine-2-carboxylate

생성물 1

HCID 445527375-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({2-[(3-hydroxyazetidin-1-yl)carbonyl]imidazo[1,2-b]pyridazin-6-yl}amino)thiophene-3-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Ethyl 6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)imidazo[1,2-b]pyridazine-2-carboxylate (33 mg, 0.07 mmol) was taken up in tetrahydrofuran and cooled to 0° C. Trimethylaluminum (0.53 ml, 1.06 mmol) was added dropwise, followed by 3-hydroxyazetidine hydrochloride (7 mg, 0.07 mmol). The reaction was stirred at 0° C. for one hour, warmed to room temperature and allowed to react overnight. The reaction was then quenched slowly with methanol, followed by stirring for 10 minutes at room temperature. The resulting mixture was filtered, washing the solids with ethyl acetate and water. The filtrate was collected, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were concentrated under and purified via flash chromatography (0-15% methanol in dichloromethane) to afford the title compound.

후처리

  1. temperaturewarmed to room temperature
  2. customto react overnight
  3. customThe reaction was then quenched slowly with methanol
  4. stirringby stirring for 10 minutes at room temperature
  5. filtrationThe resulting mixture was filtered
  6. washwashing the solids with ethyl acetate and water
  7. customThe filtrate was collected
  8. customthe phases were separated
  9. extractionthe aqueous layer was extracted with ethyl acetate
  10. concentrationThe combined organics were concentrated under and
  11. custompurified via flash chromatography (0-15% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-6c378fd4918844458bd2491ef6f67885
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08344144B2

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