HCID 71074017, compound → HCID 53372240, compound

HRID 340806Notes

Reaction equation

HRID 340806 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][C:9]([C:13]4[C:33]([F:34])=[CH:32][C:16]5[NH:17][C:18]([O:20][CH:21]6[CH2:26][CH2:25][CH:24]([C:27]([O:29]CC)=[O:28])[CH2:23][CH2:22]6)=[N:19][C:15]=5[C:14]=4[F:35])=[CH:10][CH:11]=3)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.O([Si](C)(C)C)[K]>C1COCC1.CCOC(C)=O>[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][C:9]([C:13]4[C:33]([F:34])=[CH:32][C:16]5[NH:17][C:18]([O:20][CH:21]6[CH2:22][CH2:23][CH:24]([C:27]([OH:29])=[O:28])[CH2:25][CH2:26]6)=[N:19][C:15]=5[C:14]=4[F:35])=[CH:10][CH:11]=3)[CH:6]=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 71074017HCID 71074017, compoundHCID 178504318HCID 178504318, compound

Product 1

HCID 53372240HCID 53372240, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-{[5-(1-cyclopropyl-1H-indol-5-yl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclohexanecarboxylate (0.046 g, 0.96 mmol) was dissolved in 1 mL of THF and treated with 37 mg of KOTMS (0.037 g, 0.288 mmol). The reaction mixture was stirred at ambient temperature overnight. The mixture was then diluted with EtOAc and washed with 2 N HCl. The aqueous layer was separated and further extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound. LCMS: calculated for C25H23F2N3O3 451.46, observed m/e 451.92 (MAI)+ (Rt 2.42/4 min). 1H NMR (500 MHz, CD3OD): δ7.62 (d, 1H), 7.56 (brs, 1H), 7.25-7.20 (m, 2H), 7.00-6.92 (br, 1H), 6.42 (d, 1H), 4.92 (m, 1H), 3.41 (m, 1H), 2.37 (m, 1H), 2.34-2.27 (m, 2H), 2.15-2.07 (m, 2H), 1.73-1.55 (m, 4H), 1.13-1.08 (m, 2H), 1.03-0.98 (m, 2H).

Workup

  1. washwashed with 2 N HCl
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4e31c71760994bcea96a4df591291930
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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