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Acetic Anhydride → N-(2-((4-Oxo-3-(4-(2,2,2-trifluoroethoxy)phenyl)-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)thio)ethyl)acetamide

HRID 570753
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인쇄 미리보기

반응식

HRID 570753 반응식
Cl.[NH2:2][CH2:3][CH2:4][S:5][C:6]1[N:7]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:8](=[O:15])[C:9]2[C:10](=[CH:12][S:13][CH:14]=2)[N:11]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>O1CCCC1.CN(C)C1C=CN=CC=1>[O:15]=[C:8]1[N:7]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]([F:26])([F:25])[F:27])=[CH:20][CH:21]=2)[C:6]([S:5][CH2:4][CH2:3][NH:2][C:35](=[O:37])[CH3:36])=[N:11][C:10]2=[CH:12][S:13][CH:14]=[C:9]12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86685409HCID 86685409, 화합물

생성물 1

HCID 86685411N-(2-((4-Oxo-3-(4-(2,2,2-trifluoroethoxy)phenyl)-3,4-dihydrothieno[3,4-d]pyrimidin-2-yl)thio)ethyl)acetamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 8028
Tetrahydrofuran
용매

실험 절차

2-[(2-Aminoethyl)sulfanyl]-3-[4-(2,2,2-trifluoroethoxy)phenyl]thieno[3,4-d]pyrimidin-4(3H)-one hydrochloride (0.33 g) was suspended in tetrahydrofuran (30 ml), triethylamine (0.31 ml), acetic anhydride (0.28 ml) and 4-dimethylaminopyridine (37 mg) were added successively thereto, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The extract was washed successively with saturated aqueous citric acid solution, water and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained pale-yellow solid was purified by silica gel column chromatography (ethyl acetate/hexane) to give a colorless solid. This solid was recrystallized from ethyl acetate/hexane to give the title compound (0.22 g) as a colorless solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe extract was washed successively with saturated aqueous citric acid solution, water and saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained pale-yellow solid was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customto give a colorless solid
  8. customThis solid was recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-b2c4b6f7c8d143da8873e1446c38b8a2
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09023858B2

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