Tetrabutylammonium Fluoride → HCID 25175475, compound

HRID 2190343Notes

Reaction equation

HRID 2190343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)[CH2:9][CH2:10][N:11]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)[C:12]([NH:14][C:15]2[S:16][C:17]([Cl:35])=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH:30]=[C:29]([Si](C)(C)C)[N:28]=[N:27]4)=[CH:22][CH:21]=3)[N:19]=2)=[O:13])=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:44]2[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=2)[CH2:9][CH2:10][N:11]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)[C:12]([NH:14][C:15]2[S:16][C:17]([Cl:35])=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH:30]=[CH:29][N:28]=[N:27]4)=[CH:24][CH:25]=3)[N:19]=2)=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57586411HCID 57586411, compound

Product 1

HCID 25175475HCID 25175475, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1-(3,3-bis(4-fluorophenyl)propyl)-3-(5-chloro-4-(4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)phenyl)thiazol-2-yl)-1-(2-(pyridin-2-yl)ethyl)urea 71, prepared in the previous step, at room temperature was added tetrabutylammonium fluoride (1 M in THF, 3.0 mL, 3.0 mmol). The reaction mixture was stirred at room temperature for 30 min, heated to 40° C. for 3 h, and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 30% to 70% EtOAc in hexanes) gave 1-(3,3-bis(4-fluorophenyl)propyl)-3-(5-chloro-4-(4-(1H-1,2,3-triazol-1-yl)phenyl)-1,3-thiazol-2-yl)-1-(2-(2-pyridinyl)ethyl)urea. Mass spectrum, calculated for C34H28ClF2N7OS 655.2; found 656.1 (M++1).

Workup

  1. temperatureheated to 40° C. for 3 h
  2. washThe organic phase was washed with water (1×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel (eluted with 30% to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-31136ca8fa9d433da7c86fb5f8528188
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

Loading…