Methanol → HCID 178511734、化合物

HRID 707380ノート

反応式

HRID 707380 の反応式
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[CH:14]=[CH:13]2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.CO>C(Cl)Cl.CCOC(C)=O>[N:12]1([C@H:10]2[CH2:9][C@H:8]([NH2:7])[CH2:11]2)[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[CH:13]1

参加物

6

反応物 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 178454099HCID 178454099、化合物

生成物 1

HCID 178511734HCID 178511734、化合物収率 39.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To the solution of tert-butyl(trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (294 mg, 1.02 mmol) in DCM (2.0 ml) was added trifluoroacetic acid, 99% (760 μl, 10.2 mmol). The reaction mixture was stirred at room temperature under N2 for 1 h. The solvent was evaporated and the residue was triturated with DCM three times, redissolved in DCM, and then treated with solid NaHCO3. The solid was filtered off and the filtrate concentrated in vacuo. The crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 100% EtOAc in hexane, then 15% MeOH in EtOAc, to provide trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutanamine (75 mg, 0.401 mmol, 39.2% yield) as light-yellow oil. ESI (M+1) 188.0.

後処理

  1. customThe solvent was evaporated
  2. customthe residue was triturated with DCM three times
  3. dissolutionredissolved in DCM
  4. additiontreated with solid NaHCO3
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  8. washeluting with a gradient of 0% to 100% EtOAc in hexane

出典と根拠

ORDレコード
ord-516deb8a39714743b52a3f018d74afbd
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

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