Hydrochloric Acid → HCID 25001552, compound

HRID 2239505Notes

Reaction equation

HRID 2239505 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:29][CH3:30])=[C:17]([C:20]3[CH2:21][CH2:22][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:24][CH:25]=3)[CH:18]=2)[N:13]=[N:12][C:11]=1[C:31]([NH2:33])=[O:32].[ClH:34]>CO.[OH-].[OH-].[Pd+2].[C]>[ClH:34].[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:29][CH3:30])=[C:17]([CH:20]3[CH2:21][CH2:22][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:24][CH2:25]3)[CH:18]=2)[N:13]=[N:12][C:11]=1[C:31]([NH2:33])=[O:32]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67083775HCID 67083775, compound

Product 1

HCID 25001552HCID 25001552, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(2-fluoro-4-methylphenylamino)-6-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-7-methoxycinnoline-3-carboxamide (Example 29, 0.250 g, 0.56 mmol) in MeOH (20 ml) with a few drops of c.HCl, was run through an H-Cube apparatus at 1 mL/min using a 20 wt % Pd(OH)2/Carbon cartridge at 10 bar. When the reduction was judged complete by LCMS, the solution was concentrated under reduced pressure to give 0.234 g (86%) product. 1H NMR: 12.51 (s, 1H), 10.51 (s, 1H), 8.76 (s, 1H), 8.21 (s, 1H), 7.65 (s, 1H), 7.36 (m, 3H), 7.18 (m, 1H), 4.03 (s, 3H), 3.38 (m, 1H), 3.26 (m, 2H), 3.05 (m, 3H), 2.41 (s, 3H), 1.72 (m, 2H), 1.61 (m, 2H), 1.26 (d, 6H); m/z 452.

Workup

  1. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2fb7cd3410eb4cc6882bf294253c4191
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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