N-methyl-2-pyrrolidone → HCID 58451281, compound

HRID 2366810Notes

Reaction equation

HRID 2366810 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:18]=[C:19]([NH:24]C(=O)OCC4C=CC=CC=4)[CH:20]=[CH:21][C:22]=2[CH3:23])[N:10]=3)=[O:5])[CH2:3][CH2:2]1.CN1CCCC1=O.C([O-])=O.[NH4+]>C(O)C.[C].[Pd]>[NH2:24][C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:17]([CH:18]=1)[O:16][C:11]1[N:10]=[C:9]2[S:8][C:7]([NH:6][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[N:15][C:14]2=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 2723923Ammonium formateHCID 58451271HCID 58451271, compound

Product 1

HCID 58451281HCID 58451281, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl [3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]carbamate (14.4 g, 30.3 mmol) produced in Example 33(v) in ethanol (300 mL)/1-methylpyrrolidin-2-one (100 mL) were added 10% palladium carbon (27.3 g, 25.7 mmol) and ammonium formate (61.9 g, 909 mmol), and the mixture was stirred at room temperature for 5 days under a hydrogen atmosphere (1 atm). The insoluble material was filtered off through a celite pad, and the filtrate was concentrated under reduced pressure. To the obtained solution in 1-methylpyrrolidin-2-one was added water (300 ml), and the precipitated solid was collected by filtration and washed with water (500 mL). The solid collected by filtration was dissolved in a mixture of tetrahydrofuran (800 mL)/ethyl acetate (800 mL), washed with saturated brine (2×400 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was washed successively with a mixture of tetrahydrofuran (10 mL)/diisopropyl ether (10 mL) and diisopropyl ether (40 mL) to give the title compound (7.29 g, 71%) as a white solid.

Workup

  1. filtrationThe insoluble material was filtered off through a celite pad
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the obtained solution in 1-methylpyrrolidin-2-one was added water (300 ml)
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water (500 mL)
  6. filtrationThe solid collected by filtration
  7. dissolutionwas dissolved in a mixture of tetrahydrofuran (800 mL)/ethyl acetate (800 mL)
  8. washwashed with saturated brine (2×400 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washThe obtained residue was washed successively with a mixture of tetrahydrofuran (10 mL)/diisopropyl ether (10 mL) and diisopropyl ether (40 mL)

Sources & evidence

ORD record
ord-a0f33f992cef4b19b10836ef7ea67f0d
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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