Phthalaldehydic acid → HCID 59608074, compound

HRID 1690043Notes

Reaction equation

HRID 1690043 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[CH:9]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=O.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[N+:28]#[C-:29].Cl(O)(=O)(=O)=O>C(O)C>[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[NH:28][C:29]1[N:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]2=[N:1][C:9]=1[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 8406Phthalaldehydic acidHCID 24247Perchloric AcidHCID 760092,6-Dimethylphenyl isocyanideHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 59608074HCID 59608074, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.1 0.802 g (6.8 mmol) of 2-amino-5-fluoropyridine and 0.946 g (6.3 mmol) of 2-formylbenzoic acid are dissolved successively in 20 ml of ethanol at RT under inert gas. 0.929 g (6.8 mmol) of 2,6-dimethylphenyl isocyanide are then added, 0.291 ml (3.4 mmol) of 70% perchloric acid is added dropwise, and the mixture is stirred at RT for a further 20 h. 50 ml of petroleum ether are subsequently added, the precipitated solid is filtered off with suction and washed with a little ethyl acetate, giving 1.900 g (74%) of 2-[3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridin-2-yl]benzoic acid as solid; MS-FAB (M+H+)=376.6; Rf (HPLC, polar method): 1.61 min. This is employed in the next step without further purification.

Workup

  1. filtrationthe precipitated solid is filtered off with suction
  2. washwashed with a little ethyl acetate

Sources & evidence

ORD record
ord-f3e2526e55d44e939a4a57f748f43c92
Source dataset
uspto-grants-2012_04
Patent number
US08153649B2

Reaction notes

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