Potassium trimethylsilanolate → HCID 67440573, compound

HRID 340787Notes

Reaction equation

HRID 340787 reaction equation
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:27]([F:28])=[CH:26][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:20][CH2:19][CH:18]([C:21]([O:23]CC)=[O:22])[CH2:17][CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:29])=[CH:3][CH:2]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[C:1]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:27]([F:28])=[CH:26][C:10]3[NH:11][C:12]([O:14][CH:15]4[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]4)=[N:13][C:9]=3[C:8]=2[F:29])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 67440813HCID 67440813, compound

Product 1

HCID 67440573HCID 67440573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{[5-(biphenyl-4-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclohexanecarboxylate (0.615 g, 1.291 mmol) in THF (5 ml) was added potassium trimethyl silanolate (0.550 g, 4.29 mmol). The reaction was stirred overnight at ambient temperature. Then the volatiles were removed in vacuo and the resulting residue was acidified with 1N aqueous HCl and extracted with EtOAc. The organic phase was washed with water and concentrated in vacuo. Purification of the resulting residue by reverse phase HPLC eluting with 50-100% MeCN: H2O afforded the title compound as a white solid. LC-MS: calculated for C26H22F2N2O3 448.16, observed m/e 449.01 (M+H)+ (Rt 2.32/4 min). 1H NMR (500 MHz, C2D6OS): δ 7.80-7.70 (m, 4H), 7.55-7.45 (m, 4H), 7.40 (m, 1H), 7.15 (d, 1H), 5.00-4.90 (m, 1H), 2.30 (m, 1H), 2.25 (m, 2H), 2.00 (m, 2H), 1.50 (m, 4H).

Workup

  1. customThen the volatiles were removed in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water
  4. concentrationconcentrated in vacuo
  5. customPurification of the resulting residue by reverse phase HPLC
  6. washeluting with 50-100% MeCN

Sources & evidence

ORD record
ord-9aa5d6b825ee47659f4772d9519f0ba3
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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