Tetrabutylammonium Fluoride → HCID 45256865, compound

HRID 1945300Notes

Reaction equation

HRID 1945300 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[C:21]([C:48]2[CH:53]=[CH:52][C:51]([N:54]3[CH2:58][CH2:57][CH2:56][CH2:55]3)=[CH:50][CH:49]=2)=[CH:22][C:23]2[N:27]=[C:26]([O:28][C:29]3[CH:30]=[CH:31][C:32]([CH3:38])=[C:33]([CH:37]=3)[C:34]([OH:36])=[O:35])[N:25](COCC[Si](C)(C)C)[C:24]=2[CH:47]=1>O1CCOCC1.CCOC(C)=O>[Cl:19][C:20]1[C:21]([C:48]2[CH:53]=[CH:52][C:51]([N:54]3[CH2:58][CH2:57][CH2:56][CH2:55]3)=[CH:50][CH:49]=2)=[CH:22][C:23]2[N:27]=[C:26]([O:28][C:29]3[CH:30]=[CH:31][C:32]([CH3:38])=[C:33]([CH:37]=3)[C:34]([OH:36])=[O:35])[NH:25][C:24]=2[CH:47]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68659480HCID 68659480, compound

Product 1

HCID 45256865HCID 45256865, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

TBAF (1M in THF) (0.5 mL, 0.5 mmol) was added to a solution of 5-[(6-chloro-5-(4-pyrrolidin-1-ylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoic acid in dioxane (3 mL). The reaction was heated at 80° C. for 16 h. The mixture was diluted with EtOAc (10 mL) and washed with 2N HCl, followed by water and concentrated. Purification by reverse phase HPLC eluting with 10-90% MeCN:water) afforded the title compound as an off-white solid. LC-MS: calculated for C25H22ClN3O3 447.13, observed m/e 448.04 (M+H)+ (Rt 1.80 min). 1H NMR (500 MHz, CD3OD): δ 1H NMR (500 MHz, CD3OD): δ 7.87 (s, 1H) 7.48 (s, 1H) 7.42 (m, 2H) 7.28 (s, 1H) 7.22 (m, 2H) 6.75 (m, 2H) 3.84 (s, 3H) 3.31 (m, 2H) 2.61 (s, 3H) 2.03 (m, 2H).

Workup

  1. washwashed with 2N HCl
  2. concentrationconcentrated
  3. customPurification by reverse phase HPLC
  4. washeluting with 10-90% MeCN

Sources & evidence

ORD record
ord-9180e872f8974bee8a6558d022f3b8d9
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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