Dimethyl Sulfoxide → (S)-1-(2-benzyl-4-(8-methoxy-2-(trifluoromethyl)quinolin-5-yl)piperazin-1-yl)-2-(1H-1,2,4-triazol-5-yl)ethanone

HRID 1423184Notes

Reaction equation

HRID 1423184 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:28])[F:27])=[N:19]3)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:32][C:33](=O)[CH2:34][C:35]1[NH:39][CH:38]=[N:37][N:36]=1)C.[C-]#N.[Na+].CS(C)=O>CCOC(C)=O>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:27])[F:28])=[N:19]3)[CH2:11][CH2:12][N:13]1[C:33](=[O:32])[CH2:34][C:35]1[NH:36][N:37]=[CH:38][N:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 58188941(S)-5-(3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinoline2×HCID 178470790HCID 178470790, compound

Product 1

HCID 66828497(S)-1-(2-benzyl-4-(8-methoxy-2-(trifluoromethyl)quinolin-5-yl)piperazin-1-yl)-2-(1H-1,2,4-triazol-5-yl)ethanoneYield 0.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-5-(3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinoline (Example 65, Compound 153) (100.0 mg, 0.25 mmol), (4H-[1,2,4]triazol-3-yl)-acetic acid ethyl ester (83 mg, 0.50 mmol), sodium cyanide (24 mg, 0.50 mmol), and DMSO (2 mL). The reaction mixture was heated in a heat block at 100 C for 24 h then cooled to room temperature, diluted with EtOAc, and washed with water followed by brine. The organic portion was dried over MgSO4, filtered, evaporated and purified by silica gel flash chromatography to afford product as a colorless solid (0.9 mg, 0.7%). LC/MS (Method B) 3.32 min, [m/z=510.9].

Workup

  1. temperatureThe reaction mixture was heated in a heat block at 100 C for 24 h
  2. washwashed with water
  3. dry with materialThe organic portion was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-ce5c30eb5f964c29b43a7f7b1a5de5d1
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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