Tetrabutylammonium Fluoride → HCID 86623806, compound

HRID 228337Notes

Reaction equation

HRID 228337 reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13][CH2:14][CH2:15][C:16]2[CH:31]=[CH:30][C:19]([O:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][N:22]=3)=[CH:18][CH:17]=2)[CH2:8]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:13][CH2:14][CH2:15][C:16]2[CH:31]=[CH:30][C:19]([O:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][N:22]=3)=[CH:18][CH:17]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride3×HCID 86623807HCID 86623807, compound

Product 1

HCID 86623806HCID 86623806, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Treat (±)-(cis)-6-(4-{2-[3-(tert-butyldimethyl-silyloxy)cyclohexylamino]ethyl}phenoxy)nicotinamide (56.8 mg, 0.12 mmol) in THF (1.0 mL) with 1.0 M tetrabutylammonium fluoride (TBAF) in THF (0.5 eq) for 1 hour. Add another 0.5 eq of 1.0 M TBAF and stir for 4 hours. Add 1.0 eq of 1.0 M TBAF and stir for 2.5 days. Concentrate and purify by flash chromatography, eluting with 10% (2.0 M NH3 in MeOH) in CH2Cl2. Repeat the chromatography to afford the title compound (29.9 mg, 70%): MS ES+ 356.0 (M+H)+, HRMS calcd for C21H28N3O2 356.1974 (M+H)+, found 356.1965, time 0.41 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-99% over 19 min], tR=7.11 min, 100% purity; Anal. Calcd for C20H25N3O3.0.4CH2Cl2.0.4MeOH: C, 62.11; H, 6.87; N, 10.45. Found: C, 61.95; H, 6.88; N, 10.36.

Workup

  1. stirringstir for 2.5 days
  2. concentrationConcentrate
  3. custompurify by flash chromatography
  4. washeluting with 10% (2.0 M NH3 in MeOH) in CH2Cl2

Sources & evidence

ORD record
ord-1c797991a1c249cda3860daea84aa447
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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