Water → HCID 66663086, compound

HRID 475570Notes

Reaction equation

HRID 475570 reaction equation
C1(COC2C=C(C3OC=C(C[NH:20][C:21](=[O:29])[C:22]4[C:27]([OH:28])=[CH:26][CH:25]=[CH:24][N:23]=4)N=3)C=CC=2OC)CC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][CH2:38][CH3:39].O>C(#N)C.C(OCC)(=O)C>[CH2:37]([O:28][C:27]1[C:22]([C:21]([NH2:20])=[O:29])=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:38][CH3:39]

Participants

7

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 10796Cesium carbonateHCID 68982881HCID 68982881, compound

Product 1

HCID 66663086HCID 66663086, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.1 g of N-[2-(3-cyclopropylmethoxy-4-methoxyphenyl)oxazol-4-ylmethyl]-3-hydroxypicolinamide obtained in Example 45 and 0.16 g of cesium carbonate were dissolved in 4 ml of acetonitrile, and 0.2 g of 1-bromopropane was added thereto and stirred overnight at room temperature. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The extract was washed with water once, and further washed with saturated aqueous citric acid once. The organic layer was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, yielding 72 mg of white powdery N-2-(3-cyclopropylmethoxy-4-methoxyphenyl)oxazol-4-ylmethyl]-3-propoxypicolinamide.

Workup

  1. washThe extract was washed with water once
  2. washfurther washed with saturated aqueous citric acid once
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e09308154e054a059712268fefedaaf6
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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