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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
ノート
印刷プレビュー

反応式

HRID 1972645 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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-ol2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387
N-methyl-2-pyrrolidone
溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-89692d5b59ff40779d24666984e4ef20
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431563B2

反応ノート

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