Sodium Hydroxide → HCID 136199428, compound

HRID 409555Notes

Reaction equation

HRID 409555 reaction equation
C(O)(=O)C.[CH:5](N)=[NH:6].[NH2:8][C:9]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[N:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]3=[CH:22][N:21]=2)=[O:19])=[CH:14][C:10]=1[C:11](O)=[O:12].[OH-].[Na+]>C(O)C>[CH:22]1[N:21]=[C:20]([C:18]([C:15]2[CH:14]=[C:10]3[C:9](=[CH:17][CH:16]=2)[N:8]=[CH:5][NH:6][C:11]3=[O:12])=[O:19])[N:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 160693Formamidine acetateHCID 66653420HCID 66653420, compound

Product 1

HCID 136199428HCID 136199428, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

0.36 g (3.6 mmol) of formamidine acetate is added to 0.2 g (0.72 mmol) of 2-amino-5-(imidazo[1,5-a]pyridin-3-ylcarbonyl)benzoic acid (described in WO 06/097625) in 7 ml of ethanol. The reaction medium is microwave-heated at 150° C. for 25 minutes. The reaction medium is hydrolysed with a 1N aqueous solution of sodium hydroxide. The aqueous phase is extracted with dichloromethane. The heterogeneous organic phase is filtered. The solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (90/10) mixture. 54 mg of a yellow solid are obtained.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. filtrationThe heterogeneous organic phase is filtered
  3. customThe solid obtained
  4. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-2d993ac625f34ad9a3d3aaff6b514881
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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