Potassium Carbonate → HCID 58902318, compound

HRID 1640192Notes

Reaction equation

HRID 1640192 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH:16]([C:20]([NH:22][C:23]4[CH:24]=[C:25]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=4)[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:21])[CH2:17]3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+].[N+:48]([CH2:50]S(C1C=CC(C)=CC=1)(=O)=O)#[C-:49]>CO>[O:2]1[C:1]([C:3]2[CH:8]=[C:7]([O:9][C:10]3[CH:19]=[C:18]4[C:13]([CH2:14][CH2:15][CH:16]([C:20]([NH:22][C:23]5[CH:24]=[C:25]([CH:35]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:37]=5)[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:21])[CH2:17]4)=[CH:12][CH:11]=3)[CH:6]=[CH:5][N:4]=2)=[CH:50][N:48]=[CH:49]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 58902313HCID 58902313, compound

Product 1

HCID 58902318HCID 58902318, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl [3-[({7-[(2-formylpyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalen-2-yl}carbonyl)amino]-5-(trifluoromethyl)benzyl]carbamate (120 mg, 0.21 mmol) in MeOH (2 mL), was added potassium carbonate (116 mg, 0.84 mmol) and 1-[(isocyanomethyl)sulfonyl]-4-methylbenzene (45.2 mg, 0.23 mmol). The reaction mixture was heated at 70° C. for 30 min. and then allowed to cool to rt and the solvents were evaporated. The residue was dissolved in DCM, washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl [3-{[(7-{[2-(1,3-oxazol-5-yl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalen-2-yl)carbonyl]amino}-5-(trifluoromethyl)benzyl]carbamate (95.0 mg, 74.1%). LCMS: (FA) ES+ 609.3, ES− 607.4.

Workup

  1. temperatureto cool to rt
  2. customthe solvents were evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-885e6788a62e44cfb81155a62164b7df
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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