Tetrabutylammonium Fluoride → N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-ethynyl-4-methylbenzamide

HRID 1255951Notes

Reaction equation

HRID 1255951 reaction equation
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:34])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([C:28]#[C:29][Si](C)(C)C)[CH:22]=3)=[CH:15][C:14]=2[C:35]([F:38])([F:37])[F:36])[CH2:8][CH2:7]1)([CH3:4])=[O:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:34])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([C:28]#[CH:29])[CH:22]=3)=[CH:15][C:14]=2[C:35]([F:38])([F:36])[F:37])[CH2:8][CH2:7]1)([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68911889N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide

Product 1

HCID 86632313N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-ethynyl-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide (4.1 mmol) in THF (15 mL) is added 5 mL of TBAF in THF (1.0M). After stirring at rt for 1 h, the mixture is partitioned between H2O and EtOAc. The combined organic layers are dried over Na2SO4, filtered, and then concentrated on a rotavap and the residue is purified on a silica gel column (eluent: 10% MeOH in CH2Cl2, MeOH is pre-saturated with ammonia gas).

Workup

  1. customthe mixture is partitioned between H2O and EtOAc
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated on a rotavap
  5. customthe residue is purified on a silica gel column (eluent: 10% MeOH in CH2Cl2, MeOH is pre-saturated with ammonia gas)

Sources & evidence

ORD record
ord-c3a0bc7f6c1f42e798089b66b1823287
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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