HCID 59436101, compound → HCID 59435980, compound

HRID 1802497Notes

Reaction equation

HRID 1802497 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:28])[C:11]=1[NH:12][C:13]1[C:22]2[CH:23]=[CH:24][NH:25][C:26](=[O:27])[C:21]=2[C:20]2[C:15](=[CH:16][CH:17]=[N:18][CH:19]=2)[N:14]=1)[C:5]([O:7]C)=O.[CH2:29]([Mg]Br)[CH3:30]>C1COCC1.[Ti+4]>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2([OH:7])[CH2:30][CH2:29]2)[CH:9]=[C:10]([Cl:28])[C:11]=1[NH:12][C:13]1[C:22]2[CH:23]=[CH:24][NH:25][C:26](=[O:27])[C:21]=2[C:20]2[C:15](=[CH:16][CH:17]=[N:18][CH:19]=2)[N:14]=1

Participants

5

Reactant 2

HCID 59436101HCID 59436101, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 59435980HCID 59435980, compound

Reagents, catalysts & solvents 2

HCID 114942Titanium cation (4+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3,5-dichloro-4-[(10-oxo-9,10-dihydropyrido[4,3-c]-1,6-naphthyridin-6-yl)amino]benzoate (67 mg, 0.16 mmol) and titanium (IV) isoproxide (46 mg, 0.16 mmol) in THF (4 mL) was added ethylmagnesium bromide (1.29 mL, 1.29 mmol, 1.0 M in THF) dropwise. The solution was stirred at room temperature overnight and extracted with 3:1 CHCl3/iPrOH. Column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH) afforded the title compound.

Workup

  1. extractionextracted with 3:1 CHCl3/iPrOH

Sources & evidence

ORD record
ord-ada4bdf89760415988c82e97f4079f31
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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