HCID 67083935, compound → HCID 67083714, compound

HRID 2239508Notes

Reaction equation

HRID 2239508 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:26][CH3:27])=[C:17]([C:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=3)[CH:18]=2)[N:13]=[N:12][C:11]=1[C:28]([NH2:30])=[O:29]>CO.Cl.[OH-].[OH-].[Pd+2].[C]>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:26][CH3:27])=[C:17]([CH:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[CH:18]=2)[N:13]=[N:12][C:11]=1[C:28]([NH2:30])=[O:29]

Participants

5

Reactant 1

HCID 67083935HCID 67083935, compound

Product 1

HCID 67083714HCID 67083714, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(2-fluoro-4-methylphenylamino)-7-methoxy-6-(1,2,3,6-tetrahydropyridin-4-yl)cinnoline-3-carboxamide (Example 52, 0.9 g, 2.21 mmol) in MeOH (44.2 ml) with a few drops of conc. HCl was passed through an H Cube apparatus using a 20 wt % Pd(OH)2/Carbon cartridge, at 10 bar. The solvent was removed under reduced pressure and the residue was purified with silica chromatography CH2Cl2/10% MeOH (1% NH4OH) to give 692 mg (77%) of a light yellow solid. 1H NMR: MeOD 7.61 (s, 1H), 7.37 (m, 1H), 7.23 (m, 1H), 7.12 (m, 2H), 4.09 (s, 3H), 3.38 (m, 2H), 3.22 (m, 1H), 3.12 (m, 2H), 2.43 (s, 3H), 1.90 (m, 2H), 1.36 (m, 2H); m/z 410.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified with silica chromatography CH2Cl2/10% MeOH (1% NH4OH)

Sources & evidence

ORD record
ord-e4510d9e3cf94165b825cba51b900265
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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