1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(6'-methoxy-3-methyl-5'-nitro-2,3'-bipyridin-6-yl)cyclopropanecarboxamide → N-(5'-amino-6'-methoxy-3-methyl-2,3'-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 869984Notes

Reaction equation

HRID 869984 reaction equation
[F:1][C:2]1([F:35])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[CH:24]=[N:25][C:26]([O:32][CH3:33])=[C:27]([N+:29]([O-])=O)[CH:28]=5)[C:20]([CH3:34])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.[H][H]>CO.[Pd]>[NH2:29][C:27]1[CH:28]=[C:23]([C:21]2[C:20]([CH3:34])=[CH:19][CH:18]=[C:17]([NH:16][C:14]([C:11]3([C:9]4[CH:8]=[CH:7][C:5]5[O:6][C:2]([F:1])([F:35])[O:3][C:4]=5[CH:10]=4)[CH2:12][CH2:13]3)=[O:15])[N:22]=2)[CH:24]=[N:25][C:26]=1[O:32][CH3:33]

Participants

5

Reactant 2

HCID 1176408041-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(6'-methoxy-3-methyl-5'-nitro-2,3'-bipyridin-6-yl)cyclopropanecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 25118363N-(5'-amino-6'-methoxy-3-methyl-2,3'-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamideYield 77.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6′-methoxy-3-methyl-5′-nitro-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (71 mg, 0.15 mmol) in methanol (10 mL) was added Pd/C (15 mg, 0.015 mmol) The reaction was stirred at room temperature under a balloon of hydrogen for one hour before being filtered and evaporated to yield the product (53 mg, 77%). ESI-MS m/z calc. 454.15. found 455.1 (M+1)+. Retention time 1.75 minutes.

Workup

  1. filtrationbefore being filtered
  2. customevaporated

Sources & evidence

ORD record
ord-d4ed8f728488405a879c3e504ea0b126
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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