Trifluoroacetic acid → (S)-4-(3-aminopyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60310노트

반응식

HRID 60310 반응식
[C:1]([C:3]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]3[N:20]=[CH:21][CH:22]=[C:23]([N:24]4[CH2:28][CH2:27][C@H:26]([NH:29]C(=O)OC(C)(C)C)[CH2:25]4)[C:6]=3[C:5]=2[CH:4]=1)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:29][C@H:26]1[CH2:27][CH2:28][N:24]([C:23]2[C:6]3[C:5]4[CH:4]=[C:3]([C:1]#[N:2])[N:11]=[CH:10][C:9]=4[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]=3[N:20]=[CH:21][CH:22]=2)[CH2:25]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 58365035(S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrol-4-yl)pyrrolidin-3-ylcarbamate

생성물 1

HCID 58365022(S)-4-(3-aminopyrrolidin-1-yl)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-tert-butyl 1-(6-cyano-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-4-yl)pyrrolidin-3-ylcarbamate (401 mg, 0.79 mmol) in methylene chloride (9.0 mL) was added trifluoroacetic acid (9.0 mL), and the mixture was stirred at ambient temperature for 10 minutes. The solvent was evaporated in vacuo, and the resulting residue was dissolved in methylene chloride and treated with a solution of saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo to afford the title compound as a yellow foam, which was used in the next step without any further purification (268 mg, 83%).

후처리

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe resulting residue was dissolved in methylene chloride
  3. additiontreated with a solution of saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ce98a44b267547c5b176d994fbbf4323
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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