Ammonium Hydroxide → 2-(2-(4-((6-Amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

HRID 1972646노트

반응식

HRID 1972646 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[CH:13]([C:30]#[C:31][CH3:32])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:34]>CCO>[NH2:34][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=3)[CH:13]([C:30]#[C:31][CH3:32])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 866704262-(2-(4-((6-Chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

생성물 1

HCID 569329932-(2-(4-((6-Amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol수율 79.9%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
120 °C

실험 절차

To a 330-mL pressure vessel was added 2-(2-(4-((6-chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (6.50 g, 13.3 mmol), EtOH (80 mL), and ammonium hydroxide (30%, 80.0 mL, 616 mmol, J. T. Baker, Philipsburg, N.J.). The tube was sealed and heated at 120° C. for 10 h and then the solvent was removed in vacuo. The residue was partitioned between water (100 mL) and DCM (200 mL). The aqueous layer was extracted with DCM (2×100 mL) and the combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography (330 g of silica, 1 to 5% 2 M NH3 in MeOH in DCM) to afford 2-(2-(4-((6-amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (5.0 g) as a mixture of four isomers.

후처리

  1. customThe tube was sealed
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between water (100 mL) and DCM (200 mL)
  4. extractionThe aqueous layer was extracted with DCM (2×100 mL)
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (330 g of silica, 1 to 5% 2 M NH3 in MeOH in DCM)

출처 및 근거

ORD 기록
ord-2066f7965b4f476eb6eb310f9879acb2
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431563B2

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