Lawesson's reagent → HCID 88771173, 화합물

HRID 593358노트

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HRID 593358 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([F:26])=[C:16]([C@@:18]4([CH3:25])[NH:23][C:22](=O)[CH2:21][O:20][CH2:19]4)[CH:17]=3)[CH2:7][CH2:8][C:9]=2[CH:10]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([F:26])=[C:16]([C@@:18]4([CH3:25])[NH:23][C:22](=[S:36])[CH2:21][O:20][CH2:19]4)[CH:17]=3)[CH2:7][CH2:8][C:9]=2[CH:10]=1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 68152353HCID 68152353, 화합물

생성물 1

HCID 88771173HCID 88771173, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A solution of (R)-5-[5-((RS)-3-chloro-6,7-dihydro-5H-[1]pyrindin-7-ylamino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one (76 mg, 0.2 mmol) in dioxane (3 ml) was treated with Lawesson's reagent (53.2 mg, 0.13 mmol). The reaction mixture was stirred at 80° C. for 3 hours. For the workup, the mixture was quenched with a saturated aqueous solution of sodium hydrogen carbonate, thereafter extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate, then evaporated at reduced pressure. The crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 45:55 as the eluent. The (R)-5-[5-((RS)-3-chloro-6,7-dihydro-5H-[1]pyrindin-7-ylamino)-2-fluoro-phenyl]-5-methyl-morpholin-3-thione was obtained as a white solid (58 mg, 73%); (calculated) C19H19ClFN3OS [391.90]; (found) [M+H]+=392, [M+2+H]+=394.

후처리

  1. customFor the workup, the mixture was quenched with a saturated aqueous solution of sodium hydrogen carbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. customevaporated at reduced pressure
  5. customThe crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 45:55 as the eluent

출처 및 근거

ORD 기록
ord-875e426e4b284d96a904d7a52ef7eba8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242943B2

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