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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Ethyl Acetate → 4-(4-((7R,8aS)-octahydro-5,5-dimethylindolizin-7-ylamino)-5-fluoropyrimidin-2-ylamino)-5-fluoro-2-(4,5-dihydro-4-methyl-5-oxotetrazol-1-yl)benzonitrile

HRID 633400
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HRID 633400 반응식
[CH3:1][C:2]1([CH3:35])[CH2:10][C@H:9]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]3[C:21]([F:34])=[CH:22][C:23](Br)=[C:24]([N:26]4[C:30](=[O:31])[N:29]([CH3:32])[N:28]=[N:27]4)[CH:25]=3)[N:13]=2)[CH2:8][C@H:7]2[N:3]1[CH2:4][CH2:5][CH2:6]2.[Cu][C:37]#[N:38].[Cu](C#N)C#N.C(OCC)(=O)C>CN(C)C=O>[CH3:1][C:2]1([CH3:35])[CH2:10][C@H:9]([NH:11][C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]3[C:21]([F:34])=[CH:22][C:23]([C:37]#[N:38])=[C:24]([N:26]4[C:30](=[O:31])[N:29]([CH3:32])[N:28]=[N:27]4)[CH:25]=3)[N:13]=2)[CH2:8][C@H:7]2[N:3]1[CH2:4][CH2:5][CH2:6]2
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 867044941-(5-(4-((7R,8aS)-octahydro-5,5-dimethylindolizin-7-ylamino)-5-fluoropyrimidin-2-ylamino)-2-bromo-4-fluorophenyl)-4-methyl-1H-tetrazol-5(4H)-oneHCID 178418260HCID 178418260, 화합물HCID 178418546HCID 178418546, 화합물

생성물 1

HCID 867044994-(4-((7R,8aS)-octahydro-5,5-dimethylindolizin-7-ylamino)-5-fluoropyrimidin-2-ylamino)-5-fluoro-2-(4,5-dihydro-4-methyl-5-oxotetrazol-1-yl)benzonitrile
수율 43%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

1-(5-(4-((7R,8aS)-octahydro-5,5-dimethylindolizin-7-ylamino)-5-fluoropyrimidin-2-ylamino)-2-bromo-4-fluorophenyl)-4-methyl-1H-tetrazol-5(4H)-one (54.3 mg, 0.10 mmol) was added to a tared reaction vial with magnetic stir bar and weighed. This was dissolved in 2 mL dimethylformamide and copper(I) cyanide (18.0 mg, 0.20 mmol) was weighed out and added. The reaction was heated at 100° C. for three hours, recharged with additional copper cyanide (37.7 mg, 0.42 mmol) and heated overnight at 115° C. The reaction was diluted into ethyl acetate and washed in succession with brine and water to remove DMF. The ethyl acetate layer was dried over sodium sulfate, filtered, and concentrated onto silica. Product was purified by column chromatography. After drying, 21.1 mg was obtained of the title compound (43% yield).

후처리

  1. additionadded
  2. temperatureheated overnight at 115° C
  3. washwashed in succession with brine and water
  4. customto remove DMF
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated onto silica
  8. customProduct was purified by column chromatography
  9. customAfter drying

출처 및 근거

ORD 기록
ord-8edda60660074797b30cb24d1e7a14ed
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321763B2

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