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Cyclopentanone → Cyclopentyl-[2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-amine

HRID 336480
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HRID 336480 반응식
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:16]1([NH:15][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[NH:7][C:6]([C:2]2[S:1][CH2:5][CH2:4][N:3]=2)=[CH:14]3)[CH2:20][CH2:19][CH2:18][CH2:17]1
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참가 물질

5

반응물 3

HCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 579017772-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine

생성물 1

HCID 44189667Cyclopentyl-[2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-amine수율 34%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

[2-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-amine (15 mg, 0.07 mmol) prepared in Step A was dissolved in 1,2-dichloroethane (10 mL). Cyclopentanone (12 mg, 0.14 mmol) and sodium triacetoxyborohydride (29 mg, 0.14 mmol) were added thereto, and the mixture was stirred for 3 h at room temperature. The reaction was quenched by water, and the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (6.7 mg, Yield 34%).

후처리

  1. customThe reaction was quenched by water
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-55f703dc3f004045bc09b68703c131a3
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889691B2

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