Sodium hydride → HCID 86755414, compound

HRID 1108323Notes

Reaction equation

HRID 1108323 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N+:7]([O-:11])=[CH:6][C:5]=1[Cl:12].[N+](C1C=CC([O:22][C:23]([C:25]2[CH:26]=[CH:27][C:28]([O:43][CH3:44])=[C:29]3[O:33][C:32]([CH:34]([O:36][CH:37]4[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)[CH3:35])=[CH:31][C:30]=23)=O)=CC=1)([O-])=O>CN(C)C=O>[Cl:12][C:5]1[CH2:6][N:7]([OH:11])[CH:8]=[C:9]([Cl:10])[C:4]=1[NH:3][C:23]([C:25]1[CH:26]=[CH:27][C:28]([O:43][CH3:44])=[C:29]2[O:33][C:32]([CH:34]([O:36][CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[CH3:35])=[CH:31][C:30]=12)=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70089651HCID 70089651, compoundHCID 178507846HCID 178507846, compound

Product 1

HCID 86755414HCID 86755414, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared from sodium hydride (115 mg of a 60% dispersion in oil), 4-amino-3,5-dichloropyridine-N-oxide (474 mg), 7-methoxy-2-(1-methyl-piperidin-4-yloxymethyl)-benzofuran-4-carboxylic acid 4-nitrophenyl ester (389 mg) in N,N-dimethylformamide. Purification by column chromatography eluting with 20% methanol in dichloromethane afforded the desired product as a light brown solid (106 mg).

Workup

  1. customPurification by column chromatography
  2. washeluting with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-f6a9bf89cc6d43ac8a7cb6245e59439f
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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