Trifluoroacetic acid → (S)-N-(1-(3-(4 chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2,2,2-trifluoroacetamide

HRID 2170395노트

반응식

HRID 2170395 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C@@H:17]([NH:27]C(=O)OC(C)(C)C)[CH2:18][C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)=[C:7]2[C:3]=1[C:4]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[N:5][N:6]2[CH3:35].[F:41][C:42]([F:47])([F:46])[C:43](O)=[O:44].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C@@H:17]([NH:27][C:43](=[O:44])[C:42]([F:47])([F:46])[F:41])[CH2:18][C:19]3[CH:20]=[C:21]([F:26])[CH:22]=[C:23]([F:25])[CH:24]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)=[C:7]2[C:3]=1[C:4]([NH:36][S:37]([CH3:40])(=[O:38])=[O:39])=[N:5][N:6]2[CH3:35]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 90290217(S)-tert-butyl (1-(3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

생성물 1

HCID 90281453(S)-N-(1-(3-(4 chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2,2,2-trifluoroacetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To (S)-tert-butyl (1-(3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate (57A, 3.39 g, 5.73 mmol) in DCM (5 mL) was added trifluoroacetic acid (5 mL). The reaction mixture was stirred at room temperature for 2.5 hours. Upon complete removal of the Boc protecting group, trifluoroacetic anhydride (2.02 mL, 14.31 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes. Upon completion, the reaction mixture was filtered through celite, concentrated in vacuo, taken in EtOAc, and carefully neutralized with 1M aqueous NaHCO3 until the aqueous layer was at pH 10. The organic layer was collected and the aqueous layer extracted once more with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo, and purified by silica gel column chromatography, eluting with 0-100% EtOAc in hexanes to give the title compound. MS (m/z) 588.14 [M+H]+.

후처리

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  3. filtrationUpon completion, the reaction mixture was filtered through celite
  4. concentrationconcentrated in vacuo
  5. customThe organic layer was collected
  6. extractionthe aqueous layer extracted once more with EtOAc
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by silica gel column chromatography
  11. washeluting with 0-100% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-d686f97c8c8d4245a5550ac12a9d698e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050344B2

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