Tetrabutylammonium Fluoride → HCID 86729411, compound

HRID 521237Notes

Reaction equation

HRID 521237 reaction equation
[Si]([O:8][CH2:9][CH:10]([O:12][C:13]([N:15]1[CH2:20][CH2:19][C:18]([N:24]2[CH:28]=[C:27]([C:29](=[O:31])[NH2:30])[C:26]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[N:25]2)([CH2:21][C:22]#[N:23])[CH2:17][CH2:16]1)=[O:14])[CH3:11])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)Cl>[C:29]([C:27]1[C:26]([NH:32][C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)=[N:25][N:24]([C:18]2([CH2:21][C:22]#[N:23])[CH2:17][CH2:16][N:15]([C:13]([O:12][CH:10]([CH3:11])[CH2:9][OH:8])=[O:14])[CH2:20][CH2:19]2)[CH:28]=1)(=[O:31])[NH2:30]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86729412HCID 86729412, compound

Product 1

HCID 86729411HCID 86729411, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-yl4-{4-carbamoyl-3-[(4-fluorophenyl)amino]-1H-pyrazol-1-yl}-4-(cyanomethyl)piperidine-1-carboxylate (Example 30-51) (86 mg, 0.15 mmol) in THF (1.0 mL) was added a solution of TBAF.3H2O (316 mg, 1.00 mmol) in THF (1.0 mL). The resulting mixture was allowed to stir at ambient temperature for 3 hours. The mixture was then diluted with DCM, washed with water, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by MPLC on silica gel (using a gradient elution of 0-20% MeOH/DCM) to afford the title compound, Example #31.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by MPLC on silica gel (
  6. washa gradient elution of 0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-03253288c3514a1fbbacd086782ef48e
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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