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Diisopropylethylamine → 2-(2-(4-((6-Chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

HRID 1972645
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HRID 1972645 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][NH:14][CH:13]([C:17]#[C:18][CH3:19])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:30]1[N:35]=[CH:34][C:33]([C:36]([OH:42])([CH3:41])[C:37]([F:40])([F:39])[F:38])=[CH:32][N:31]=1>CN1C(=O)CCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:30]3[N:31]=[CH:32][C:33]([C:36]([OH:42])([CH3:41])[C:37]([F:38])([F:39])[F:40])=[CH:34][N:35]=3)[CH:13]([C:17]#[C:18][CH3:19])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 772307671-((6-Chloro-3-pyridinyl)sulfonyl)-3-(1-propyn-1-yl)piperazineHCID 866703602-(2-Chloropyrimidin-5-yl)-1,1,1-trifluoropropan-2-ol2회

생성물 1

HCID 866704262-(2-(4-((6-Chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol수율 48.1%

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
140 °C

실험 절차

To a 20 mL vial was added 1-((6-chloro-3-pyridinyl)sulfonyl)-3-(1-propyn-1-yl)piperazine (1.70 g, 7.47 mmol, Example 240, Step 4), diisopropylethylamine (4.20 mL, 24.2 mmol), and NMP (8.0 mL), and 2-(2-chloro-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (1.4 g, 6.37 mmol, Intermediate E). The vial was sealed and heated at 140° C. for 9 h. The reaction mixture was cooled to rt and partitioned between EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted with EtOAc (2×75 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography (120 g of silica, 10 to 50% EtOAc in hexanes) to afford 2-(2-(4-((6-chloro-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (1.5 g) as a light yellow solid.

후처리

  1. customThe vial was sealed
  2. temperatureThe reaction mixture was cooled to rt
  3. custompartitioned between EtOAc (200 mL) and water (100 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×75 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 (120 g of silica, 10 to 50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-89692d5b59ff40779d24666984e4ef20
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431563B2

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