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Sodium hydride → 5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide

HRID 385874
Notes
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Reaction equation

HRID 385874 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1.Cl[CH2:32][C:33]1[O:34][C:35]([CH3:38])=[N:36][N:37]=1>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:11])[CH3:12])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][CH2:32][C:33]3[O:34][C:35]([CH3:38])=[N:36][N:37]=3)[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazoleHCID 251234855-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-(hydroxymethyl)-2-pyridinyl)amino)-3-thiophenecarboxamide

Product 1

HCID 595260635-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (14 mg, 0.35 mmol) in DMF (1.75 mL) at 0° C. under argon was added 5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(hydroxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (Example 43) (70 mg, 0.17 mmol) and the mixture was allowed to stir for 10 minutes. 2-(Chloromethyl)-5-methyl-1,3,4-oxadiazole (35 mg, 0.26 mmol) was then added and the reaction was allowed to warm to room temperature overnight. The reaction was then quenched by the addition of water, extracted with ethyl acetate and concentrated in vacuo. The crude residue was reverse phase HPLC (acteonitrile/water with formic acid as a modifier) to afford the title compound.

Workup

  1. customThe reaction was then quenched by the addition of water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b15539a6a0534b5fa6f23f9dedf8e208
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367706B2

Reaction notes

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