Potassium Carbonate → HCID 86649036, compound

HRID 1691426Notes

Reaction equation

HRID 1691426 reaction equation
[F:1][C:2]([F:39])([F:38])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:19]3[C:20]([C:24]#[C:25][Si](C)(C)C)=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]3[N:30]=[C:31]([C:34]([F:37])([F:36])[F:35])[CH:32]=[CH:33][C:15]=3[CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:24]([C:20]1[C:19]2[N:13]([S:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:38])([F:39])[F:1])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH2:14][C:15]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[N:30][C:16]=3[NH:17][C:18]=2[CH:23]=[CH:22][CH:21]=1)#[CH:25]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86649037HCID 86649037, compound

Product 1

HCID 86649036HCID 86649036, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-7-[(trimethylsilyl)ethynyl]-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (414 mg, 0.75 mmol) in MeOH (40 mL) was added K2CO3 (306 mg, 3.00 mmol). The reaction was stirred at rt for 1.5 h, diluted with H2O, and the product was extracted with EtOAc. The combined organic extracts were washed with H2O, brine, dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography to give the title compound. 1H NMR (500 MHz, (CD3)2CO): δ 8.50 (s, 1H), 7.76 (d, 1H), 7.40 (m, 4H), 7.27 (m, 1H), 7.15 (d, 3H), 5.27 (d, 1H), 4.70 (d, 1H), 3.81 (s, 1H). LCMS: m/z 514.1 (m+H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe combined organic extracts were washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bcc764d36c2f49beb99e1f860b4e3acb
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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