Tetrabutylammonium Fluoride → HCID 49763221, compound

HRID 2188576Notes

Reaction equation

HRID 2188576 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[C:6]([NH:8][CH2:9][C:10](=[O:33])[NH:11][CH:12]1[CH2:15][N:14]([CH:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH:26]=[C:25]([C:27]#[C:28][Si](C)(C)C)[CH:24]=[N:23]3)[CH2:18][CH2:17]2)[CH2:13]1)=[O:7].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:27]([C:25]1[CH:24]=[N:23][N:22]([CH:19]2[CH2:20][CH2:21][CH:16]([N:14]3[CH2:15][CH:12]([NH:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]4[CH:34]=[CH:35][CH:36]=[C:3]([C:2]([F:38])([F:1])[F:37])[CH:4]=4)=[O:33])[CH2:13]3)[CH2:17][CH2:18]2)[CH:26]=1)#[CH:28]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 46927118HCID 46927118, compound

Product 1

HCID 49763221HCID 49763221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Trifluoromethyl-N-({1-[4-(4-trimethylsilanylethynyl-pyrazol-1-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-benzamide (as prepared in Example 29, 52.5 mg, 0.09 mmol) in THF (4 mL) was added TBAF (Aldrich, 47 mg, 0.18 mmol) and the reaction was stirred at RT over night followed by column chromatography purification (0-100% ethyl acetate in hexanes with 7N NH3 in MeOH) resulting in the title compound as a white solid.

Workup

  1. customfollowed by column chromatography purification (0-100% ethyl acetate in hexanes with 7N NH3 in MeOH)

Sources & evidence

ORD record
ord-feaefef960b14638b2e7fd2ff41fccab
Source dataset
uspto-grants-2012_12
Patent number
US08324186B2

Reaction notes

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