Trifluoroacetic acid → 6-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-methyl-5-{[(3S)-3-methyl-1-piperazinyl]methyl}-2-pyridinyl)-3-pyridinecarboxamide

HRID 644772노트

반응식

HRID 644772 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:40])[C:18]3[N:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[C@@H:27]([CH3:38])[CH2:26]4)=[C:20]([CH3:39])[CH:19]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]([CH3:40])[C:18]3[CH:19]=[C:20]([CH3:39])[C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]4)=[CH:22][N:23]=3)=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 592621991,1-Dimethylethyl (2S)-4-({6-[({6-[(4-fluorophenyl)oxy]-3-pyridinyl}carbonyl)(methyl)amino]-4-methyl-3-pyridinyl}methyl)-2-methyl-1-piperazinecarboxylate

생성물 1

HCID 237289156-[(4-Fluorophenyl)oxy]-N-methyl-N-(4-methyl-5-{[(3S)-3-methyl-1-piperazinyl]methyl}-2-pyridinyl)-3-pyridinecarboxamide수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1,1-Dimethylethyl (2S)-4-({6-[({6-[(4-fluorophenyl)oxy]-3-pyridinyl}carbonyl)(methyl)amino]-4-methyl-3-pyridinyl}methyl)-2-methyl-1-piperazinecarboxylate (D118) (26 mg, 0.047 mmol) was dissolved in dry DCM (4 mL). TFA (1 mL) was added and the reaction mixture was stirred at room temperature, under argon. The reaction mixture was concentrated, re-dissolved in methanol (2 mL) and loaded on to a 1 g SCX cartridge. Elution with methanol (20 mL) followed by 2M NH3 in methanol (20 mL) gave a colourless oil. The product was further purified by MDAP. The resulting oil was dissolved in methanol (1 mL) and loaded on to a 1 g SCX cartridge and eluted with methanol (20 mL), followed by 2M NH3 in methanol (20 mL) to give the title compound as a colourless oil (15 mg). MS (ES): MH+ 450.1.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionre-dissolved in methanol (2 mL)
  3. washElution with methanol (20 mL)
  4. customgave a colourless oil
  5. customThe product was further purified by MDAP
  6. dissolutionThe resulting oil was dissolved in methanol (1 mL)
  7. washeluted with methanol (20 mL)

출처 및 근거

ORD 기록
ord-958e04bf831f458984bb86a05478ebc7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700599B2

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