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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
Notes
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Reaction equation

HRID 1972645 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
140 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-89692d5b59ff40779d24666984e4ef20
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431563B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes