Methanesulfonic Acid → Linaprazan mesylate

HRID 2373197Notes

Reaction equation

HRID 2373197 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][C:7]([C:20]([NH:22][CH2:23][CH2:24][OH:25])=[O:21])=[CH:6][N:5]2[C:26]=1[CH3:27].[CH3:28][S:29]([OH:32])(=[O:31])=[O:30]>C(O)C>[S:29]([OH:32])(=[O:31])(=[O:30])[CH3:28].[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][C:7]([C:20]([NH:22][CH2:23][CH2:24][OH:25])=[O:21])=[CH:6][N:5]2[C:26]=1[CH3:27]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 9951066Linaprazan

Product 1

HCID 11248232Linaprazan mesylateYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

110 g 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-N-hydroxyethyl-imidazo[1,2-a]pyridine-6-carboxamide was suspended in 550 ml ethanol. 32 g methanesulphonic acid, diluted with 80 ml ethanol was charged. After rinsing with ethanol (30 ml), the suspension was stirred at room temperature until conversion to 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-N-hydroxyethyl-imidazo[1,2-a]pyridine-6-carboxamide mesylate salt form B was complete. The suspension was cooled to 2° C. at −10° C./h. The crystals were isolated and vacuum dried over the night at 30° C. 133 g of 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-N-hydroxyethyl-imidazo[1,2-a]pyridine-6-carboxamide mesylate salt form B was obtained.

Workup

  1. additionwas charged
  2. washAfter rinsing with ethanol (30 ml)
  3. temperatureThe suspension was cooled to 2° C. at −10° C./h
  4. customThe crystals were isolated
  5. customvacuum dried over the night at 30° C

Sources & evidence

ORD record
ord-4bfc1095d84d4c32997f792dc6c9dbe1
Source dataset
uspto-grants-2008_12
Patent number
US07459463B2

Reaction notes

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