Trifluoroacetic acid → [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-pyridin-3-ylmethyl)-amine

HRID 509989노트

반응식

HRID 509989 반응식
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([Cl:17])[CH:16]=[C:11]2[C:10]([CH2:18][C:19]2[C:20]([F:41])=[N:21][C:22]([N:25](C(OC(C)(C)C)=O)[CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[C:31]([F:33])[CH:32]=3)=[CH:23][CH:24]=2)=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:17][C:15]1[CH:16]=[C:11]2[C:10]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[C:31]([F:33])[CH:32]=4)=[N:21][C:20]=3[F:41])=[CH:9][NH:8][C:12]2=[N:13][CH:14]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 58259261HCID 58259261, 화합물

생성물 1

HCID 52935810[5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-pyridin-3-ylmethyl)-amine수율 53.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 3-{6-[tert-butoxycarbonyl-(5-fluoro-pyridin-3-ylmethyl)-amino]-2-fluoro-pyridin-3-ylmethyl}-5-chloro-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (144, 0.280 g, 0.478 mmol) in 10.0 mL of dichloromethane, trifluoroacetic acid (1.00 mL, 13.0 mmol) was added and the reaction stirred at room temperature overnight. This was pooled with a separate reaction run similarly and concentrated under vacuum. The resulting material was combined with aqueous potassium carbonate and ethyl acetate and mixed. The aqueous layer was separated and the organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (P-2001, 99 mg). MS (ESI) [M+H+]+=386.0.

후처리

  1. customThis was pooled with a separate reaction
  2. concentrationconcentrated under vacuum
  3. additionmixed
  4. customThe aqueous layer was separated
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with 20% ethyl acetate in hexane
  10. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-962bcb7cf9b24086a1921c8f5228ffb4
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

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