Hydrochloric Acid → HCID 58902444, compound

HRID 1640189Notes

Reaction equation

HRID 1640189 reaction equation
[C: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)#N.C[O-:43].[Na+].Cl.[C:46]([O-])(O)=[O:47].[Na+]>CO>[C:30]([O:29][C:28]([NH:27][CH2:26][C:25]1[CH:24]=[C:23]([NH:22][C:20]([CH:16]2[CH2:17][C:18]3[CH:19]=[C:10]([O:9][C:7]4[CH:6]=[CH:5][N:4]=[C:3]([C:1]([O:47][CH3:46])=[O:43])[CH:8]=4)[CH:11]=[CH:12][C:13]=3[CH2:14][CH2:15]2)=[O:21])[CH:37]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:35]=1)=[O:34])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 58902382HCID 58902382, compound

Product 1

HCID 58902444HCID 58902444, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl [3-[({7-[(2-cyanopyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalen-2-yl}carbonyl)amino]-5-(trifluoromethyl)benzyl]carbamate (2.00 g, 3.53 mmol) in MeOH (32 mL), was added a 25% solution of sodium methoxide in MeOH (0.402 mL, 1.76 mmol). The reaction mixture was heated at 65° C. for 90 min, then allowed to cool to rt. After the addition of 1N HCl solution (20.0 mL), the reaction mixture was allowed to stir at rt for 3 h. The mixture was basified by the addition of saturated NaHCO3 and the MeOH was evaporated. The mixture was extracted with EtOAc and the organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated to give methyl 4-{[7-({[3-{[(tert-butoxycarbonyl)amino]methyl}-5-(trifluoromethyl)phenyl]-amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}pyridine-2-carboxylate (2.08 g, 98.3%). LCMS: (FA) ES+ 600.3, ES− 598.4.

Workup

  1. temperatureto cool to rt
  2. customthe MeOH was evaporated
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29eeb3e503ab430cb3b889760381f265
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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