4-Methylmorpholine → HCID 58886660, compound

HRID 494707Notes

Reaction equation

HRID 494707 reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]1[C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[Cl:21])=[C:11]([Cl:22])[C:10]([NH:23][CH2:24][CH:25]([OH:27])[CH3:26])=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6](=[O:28])[C:7]1[C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[Cl:21])=[C:11]([Cl:22])[C:10]([NH:23][CH2:24][C:25](=[O:27])[CH3:26])=[N:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 79724-MethylmorpholineHCID 58886645HCID 58886645, compound

Product 1

HCID 58886660HCID 58886660, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-bromo-2-chlorophenylamino)-5-chloro-6-(2-hydroxypropylamino)-nicotinic acid tert-butyl ester (0.28 g, 0.57 mmol) in acetonitrile (1.1 mL) was added 4A molecular sieves and N-methylmorpholine (0.10 g, 0.85 mmol). The mixture was cooled to 0° C. and tetrapropylammonium perruthenate (0.030 g, 0.085 mmol) was added. After stirring for one hour, the reaction was filtered through a plug of silica gel, washing with EtOAc. The filtrate was concentrated. Purification by flash column chromatography (20:1 hexanes/ethyl acetate) provided the desired product as a white solid (86 mg, 31%). MS APCI (+) m/z 490, 492 (M+, Cl, Br pattern) detected.

Workup

  1. filtrationthe reaction was filtered through a plug of silica gel
  2. washwashing with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customPurification by flash column chromatography (20:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-3f52b0a21e1c481abc6d3565bc5b40fc
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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