Hydrochloric Acid → 2-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]thieno[2,3-b]pyridine-5-carboxylic acid

HRID 240890노트

반응식

HRID 240890 반응식
O[Li].O.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:30]([F:33])([F:32])[F:31])[O:16][N:15]=[C:14]([C:17]3[S:29][C:20]4=[N:21][CH:22]=[C:23]([C:25]([O:27]C)=[O:26])[CH:24]=[C:19]4[CH:18]=3)[CH2:13]2)[CH:8]=[C:9]([Cl:11])[CH:10]=1.Cl>O.C1COCC1>[Cl:11][C:9]1[CH:8]=[C:7]([C:12]2([C:30]([F:32])([F:31])[F:33])[O:16][N:15]=[C:14]([C:17]3[S:29][C:20]4=[N:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[CH:24]=[C:19]4[CH:18]=3)[CH2:13]2)[CH:6]=[C:5]([Cl:4])[CH:10]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 71469063Methyl 2-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)thieno[2,3-b]pyri dine-5-carboxylate

생성물 1

HCID 714691762-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]thieno[2,3-b]pyridine-5-carboxylic acid수율 73.9%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

Add a solution of LiOH—H2O (76 mg, 2 mmol) in water (0.5 mL) to a solution of methyl 2-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)thieno[2,3-b]pyri dine-5-carboxylate (237 mg, 0.5 mmol) in THF (3 mL). Stir the mixture at temperature for 12 hours. After addition of 10 mL of water, acidify the mixture with concentrated HCl to PH=6˜7. Extract the resultant mixture with ethyl acetate (3×10 mL). The combined organic layers are washed brine, dried over anhydrous Na2SO4 and concentrated under vacuum to afford 2-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-thieno[2,3-b]pyridine-5-carboxylic acid as pale yellow solid (170 mg, 73.9%), which is used in next step without further purification. MS (m/z): 461 (M+1).

후처리

  1. extractionExtract the resultant mixture with ethyl acetate (3×10 mL)
  2. washThe combined organic layers are washed brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-bdaba8d7e780490e92690b67b0608e30
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648081B2

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