Methanesulfonic Acid → Linaprazan mesylate

HRID 2373198Notes

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

Conditions

Temperature: 10 °C

Procedure

75 g 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-N-hydroxyethyl-imidazo[1,2-a]pyridine-6-carboxamide was suspended in 350 ml ethanol and cooled to 10° C. 21.9 g methanesulfonic acid, diluted with 56 ml ethanol was charged. After rinsing with ethanol (44 ml), the suspension was stirred 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 crystals of 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-N-hydroxyethyl-imidazo[1,2-a]pyridine-6-carboxamide mesylate salt form B were isolated and vacuum dried at 30° C. over night. Yield 99%.

Workup

additionwas charged
washAfter rinsing with ethanol (44 ml)

Sources & evidence

ORD record: ord-4b2e14b567044683b83d21e7592c3080
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459463B2

Reaction notes

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