p-Toluenesulfonic acid → HCID 59333289, compound

HRID 1893456Notes

Reaction equation

HRID 1893456 reaction equation
[C:1]([C:3]1[N:7]2[C:8]3[C:13]([N:14]=[C:15]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])[C:6]2=[N:5][CH:4]=1)=[CH:12][C:11]([C:21]([F:24])([F:23])[F:22])=[CH:10][CH:9]=3)#[CH:2].[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Na]>ClCCl>[C:1]([C:3]1[N:7]2[C:8]3[C:13]([N:14]=[C:15]([NH:16][CH2:17][CH2:18][CH2:19][O:20][CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30][O:25]4)[C:6]2=[N:5][CH:4]=1)=[CH:12][C:11]([C:21]([F:22])([F:23])[F:24])=[CH:10][CH:9]=3)#[CH:2]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 5360545SodiumHCID 59333283HCID 59333283, compound

Product 1

HCID 59333289HCID 59333289, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-{[1-ethynyl-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol as prepared in example 30 (334 mg, 1.0 mmol) in anhydrous dichloromethane (10 mL) cooled at 0° C., were added 3,4-dihydro-2H-pyran (109 μL, 1.2 mmol) and para-toluenesulfonic acid (19 mg, 0.1 mmol). The mixture was stirred at room temperature overnight and then poured onto a saturated aqueous solution of sodium hydrogenocarbonate and extracted twice with dichloromethane. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (silica gel, dichloromethane/methanol 20/1) to afford the title compound (302 mg, 72%) as a white solid.

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (silica gel, dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-832cd555f6fe43928c6798f256f01673
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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