Thioacetic acid → HCID 90199365, 화합물

HRID 524905

반응식

HRID 524905 반응식
C(OC(/N=N/C(=O)OC(C)C)=O)(C)C.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([F:29])[C:21]=1[N:22]1[CH2:27][CH2:26][CH:25](O)[CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49](=[O:52])([SH:51])[CH3:50]>C1COCC1.C(OC(=O)C)C>[C:49](=[O:52])([S:51][CH:25]1[CH2:26][CH2:27][N:22]([C:21]2[C:20]([F:29])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:15])[CH2:23][CH2:24]1)[CH3:50]

참가 물질

7

반응물 4

HCID 10484Thioacetic acidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86720960HCID 86720960, 화합물

생성물 1

HCID 90199365HCID 90199365, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

isopropyl (NE)-N-isopropoxycarbonyliminocarbamate (723.1 mg, 3.576 mmol) was added dropwise to a solution of 1-(3-chloro-5-fluoro-4-pyridyl)piperidin-4-ol (750 mg, 3.251 mmol) and Triphenylphosphine (937.9 mg, 828.5 μL, 3.576 mmol) in THF at −20° C. After stirring for 15 mins, ethanethioic S-acid (272.2 mg, 255.6 μL, 3.576 mmol) was added, the mixture was allowed to warm to room temperature and was stirred for a further 30 minutes. The mixture was then diluted with ethylacetate (30 ml), washed twice with water (20 ml) and with brine. The organic layer was dried with MgSO4 and concentrated in vacuo to a yellow solid that was purified by column chromatography eluting with 5/95 ether/pet ether to elute side products and then 10/90 ether/pet ether. The relevant fractions were combined and concentrated in vacuo to afford S-(1-(3-chloro-5-fluoropyridin-4-yl)piperidin-4-yl) ethanethioate as a green solid. MS (ES+) 289.0.

후처리

  1. stirringwas stirred for a further 30 minutes
  2. washwashed twice with water (20 ml) and with brine
  3. dry with materialThe organic layer was dried with MgSO4
  4. concentrationconcentrated in vacuo to a yellow solid
  5. customthat was purified by column chromatography
  6. washeluting with 5/95 ether/pet ether
  7. washto elute side products
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-084a3e97478741ebbc630aeacb88ad29
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340546B2

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