Methanol → N-{3-[(5-aminopyridin-2-yl)oxy]-4-methoxyphenyl}-3-(1-cyanocyclopropyl)benzamide

HRID 1800423Notes

Reaction equation

HRID 1800423 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][N:22]=3)[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].CO>O1CCCC1.[C].[Pd]>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:30]=[CH:31][CH:32]=[C:6]([C:3]4([C:1]#[N:2])[CH2:5][CH2:4]4)[CH:7]=3)[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])=[N:22][CH:23]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 684192063-(1-cyanocyclopropyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Product 1

HCID 68418573N-{3-[(5-aminopyridin-2-yl)oxy]-4-methoxyphenyl}-3-(1-cyanocyclopropyl)benzamideYield 102.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyanocyclopropyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (4.30 g, 9.99 mmol) in tetrahydrofuran (100 mL) were added methanol (50 mL) and 10% palladium-carbon (982 mg), and the mixture was stirred at room temperature for 14 hr under a hydrogen atmosphere (2.5 atm). The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (4.1 g) as a brown syrup substance. The syrup substance was used for the next reaction without further purification.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5196e962a4c84675aec31fd9f01900cf
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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