Tetrabutylammonium Fluoride → 6-(((2S,4R)-1-acetyl-6-ethynyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile

HRID 628952

반응식

HRID 628952 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[C:15][Si](C)(C)C)=[CH:11][CH:12]=2)[C@H:7]([NH:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)[CH2:6][C@@H:5]1[CH3:29])(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]#[CH:15])=[CH:11][CH:12]=2)[C@H:7]([NH:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)[CH2:6][C@@H:5]1[CH3:29])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 709781736-(((2S,4R)-1-Acetyl-2-methyl-6-((trimethylsilyl)ethynyl)-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile

생성물 1

HCID 867120316-(((2S,4R)-1-acetyl-6-ethynyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-(((2S,4R)-1-Acetyl-2-methyl-6-((trimethylsilyl)ethynyl)-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile (for a preparation see Intermediate 10) (1.69 g, 4.20 mmol) was treated with tetrabutylammonium fluoride (1M in THF, 4.62 ml, 4.62 mmol) and THF (18 ml) and the solution stirred at ambient conditions for 30 min. The reaction was concentrated in vacuo, diluted with water (25 ml) and extracted with DCM (3×30 ml). The organics were combined, being dried (hydrophobic frit) and the solvent evaporated in vacuo. The residue was purified by chromatography on a silica cartridge (100 g) eluting with an ethyl acetate/cyclohexane gradient (0-75%). The appropriate fractions were collected and the solvent evaporated in vacuo to give 6-(((2S,4R)-1-acetyl-6-ethynyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)nicotinonitrile (990 mg) as a yellow foam. LCMS (formate), Rt 0.92 min, MH+ 331.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with water (25 ml)
  3. extractionextracted with DCM (3×30 ml)
  4. custombeing dried (hydrophobic frit)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by chromatography on a silica cartridge (100 g)
  7. washeluting with an ethyl acetate/cyclohexane gradient (0-75%)
  8. customThe appropriate fractions were collected
  9. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-43f9a16c5b5a45bab8035f16c9c84b89
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315487B2

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