HCID 86589895, compound → HCID 67329510, compound

HRID 1675801Notes

Reaction equation

HRID 1675801 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[O:11])[C:5]=1[OH:26])=[N+]=[N-]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:17][CH:18]=2)=[O:11])[C:5]=1[OH:26]

Participants

4

Reactant 1

HCID 86589895HCID 86589895, compound

Product 1

HCID 67329510HCID 67329510, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To 0.14 g of 4-azido-3-hydroxy-N-para-phenoxyphenylpicolinamide (obtained from the compound of the Preparation Example according to the methods described in Examples a) to g)) dissolved in a mixture of ethanol/ethyl acetate, 1:2, there is added a spatula tip of 10% palladium on carbon. Hydrogenation is carried out at 20 bars pressure and ambient temperature for 4-5 hours. After filtration, concentration and chromatography of the residue in ethyl acetate, there is obtained 0.099 g of a white solid (MP : 197° C.).

Workup

  1. filtrationAfter filtration, concentration and chromatography of the residue in ethyl acetate

Sources & evidence

ORD record
ord-668c125daf4e40e7ba17a09a0f0fea83
Source dataset
uspto-grants-2011_08
Patent number
US08003799B2

Reaction notes

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