Tetrabutylammonium Fluoride → HCID 45256864, compound

HRID 1945312Notes

Reaction equation

HRID 1945312 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[C:21]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][C:49]=2[F:56])=[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>[Cl:19][C:20]1[C:21]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][C:49]=2[F:56])=[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

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68659477HCID 68659477, compound

Product 1

HCID 45256864HCID 45256864, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

TBAF (1M in THF) (0.5 mL) was added to a solution of 5-[(6-chloro-5-(2-fluoro-4-methoxyphenyl)-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. Volatiles were removed and the residue acidified with 2N aqueous HCl and extracted with EtOAc. The organic phase was washed with water and concentrated. Purification by reverse phase HPLC eluting with 15-90% MeCN:water afforded the title compound as a white solid. LC-MS: calculated for C27H36ClFN2O4 426.08, observed m/e 427.00 (M+H)+ (Rt 1.90 min). 1 H NMR (500 MHz, CD3OD): δ 7.87 (s, 1H) 7.48 (s, 1H) 7.42 (m, 2H) 7.28 (s, 1H) 7.20 (m, 1 H) 6.80 (dd, 1H) 6.75 (dd, 1H) 3.84 (s, 3H) 2.61 (s, 3H).

Workup

  1. customVolatiles were removed
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water
  4. concentrationconcentrated
  5. customPurification by reverse phase HPLC
  6. washeluting with 15-90% MeCN

Sources & evidence

ORD record
ord-e88593b4bcd84b9c8b3a609ef6c9674f
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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