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 509989ノート

反応式

HRID 509989 の反応式
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

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 58259261HCID 58259261、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-962bcb7cf9b24086a1921c8f5228ffb4
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

読み込み中…