Dimethylformamide → N1-Cyclopropyl-5-({2-[(cyclopropylcarbonyl)amino]-4-pyridyl}oxy)-1H-1-indolecarboxamide

HRID 387828Notes

Reaction equation

HRID 387828 reaction equation
[CH:1]1([NH:4][C:5]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:17]4[CH:22]=[CH:21][N:20]=[C:19]([N:23](C(C5CC5)=O)[C:24]([CH:26]5[CH2:28][CH2:27]5)=[O:25])[CH:18]=4)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[O:6])[CH2:3][CH2:2]1.[Cl-].[NH4+].CN(C)C=O>C(OCC)(=O)C.O.C(O)C>[CH:1]1([NH:4][C:5]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:17]4[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]([CH:26]5[CH2:28][CH2:27]5)=[O:25])[CH:18]=4)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22936650HCID 22936650, compound

Product 1

HCID 58930818N1-Cyclopropyl-5-({2-[(cyclopropylcarbonyl)amino]-4-pyridyl}oxy)-1H-1-indolecarboxamideYield 41%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N1-Cyclopropyl-5-({2-[di(cyclopropylcarbonyl)amino]-4-pyridyl}oxy)-1H-1-indolecarboxamide (190 mg), ammonium chloride (660 mg), dimethylformamide (5 ml), water (5 ml) and ethanol (5 ml) were stirred at 100° C. for 1 hour. Water and ethyl acetate were added for extraction, and the extract was washed 6 times with water. After drying over magnesium sulfate, the drying agent was filtered off and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and the precipitated solid was filtered out to obtain 66 mg of a white powder.

Workup

  1. washthe extract was washed 6 times with water
  2. dry with materialAfter drying over magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionEthyl acetate was added to the residue
  6. filtrationthe precipitated solid was filtered out

Sources & evidence

ORD record
ord-1a9758f9cbef4401a341bf3b5d9e696c
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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