Tetrabutylammonium Fluoride → HCID 72725463, compound

HRID 591358Notes

Reaction equation

HRID 591358 reaction equation
[Si]([O:8][CH:9]1[CH2:36][CH2:35][C:12]2[N:13]=[C:14]([NH:16][C:17]([N:19]3[CH2:24][CH2:23][CH:22]([N:25]4[C:33]5[C:28](=[CH:29][CH:30]=[C:31]([F:34])[CH:32]=5)[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)=[O:18])[S:15][C:11]=2[CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.O>C1COCC1>[F:34][C:31]1[CH:32]=[C:33]2[C:28]([CH2:27][CH2:26][N:25]2[CH:22]2[CH2:21][CH2:20][N:19]([C:17]([NH:16][C:14]3[S:15][C:11]4[CH2:10][CH:9]([OH:8])[CH2:36][CH2:35][C:12]=4[N:13]=3)=[O:18])[CH2:24][CH2:23]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 22728543Water ethylacetateHCID 89612622HCID 89612622, compound

Product 1

HCID 72725463HCID 72725463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(6-((tert-butyldimethylsilyl)oxy)-4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)-4-(6-fluoroindolin-1-yl)piperidine-1-carboxamide (106 mg, 0.2 mmol) in THF (3 mL) was added TBAF solution (1.0 M in THF, 0.8 mL, 0.8 mmol, 4 equiv) at room temperature. The resulting mixture was stirred at room temperature for 24 h and was poured into EtOAc/H2O (20 mL/20 mL). The organic layer was washed with brine (20 mL), dried (Na2SO4), and filtered. The solvent was removed by roto-evaporator and the resulting residue purified by column using 70-90% EtOAc/hexane as the eluent to yield 4-(6-fluoroindolin-1-yl)-N-(6-hydroxy-4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)piperidine-1-carboxamide as a white solid.

Workup

  1. washThe organic layer was washed with brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe solvent was removed by roto-evaporator
  5. customthe resulting residue purified by column

Sources & evidence

ORD record
ord-a577240611ba4bcaa79ef2f4fca3c258
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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