Methanesulfonic Acid → ethyl 3-[[2-[[4-[(Z)-N'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate;methanesulfonic acid

HRID 1470525Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:8]([C:10]1[CH:39]=[CH:38][C:13]2[N:14]([CH3:37])[C:15]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[NH:36])[NH:26][C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:28])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9].[CH3:47][S:48]([OH:51])(=[O:50])=[O:49]>CC(C)=O>[CH3:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][C:27](/[N:26]=[C:25](\[NH2:36])/[C:22]1[CH:21]=[CH:20][C:19]([NH:18][CH2:17][C:15]2[N:14]([CH3:37])[C:13]3[CH:38]=[CH:39][C:10]([C:8]([N:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:9])=[CH:11][C:12]=3[N:16]=2)=[CH:24][CH:23]=1)=[O:28].[CH3:47][S:48]([OH:51])(=[O:50])=[O:49]

Participants

Conditions

Temperature: 20 °C

Procedure

100 g of 1-methyl-2-[N-[4-(N-n-hexyloxycarbonylamidino)phenyl]amino methyl]benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl) amide was dissolved in 890 ml of acetone under heating. A solution of 15 g of methane sulfonic acid in 200 ml of acetone was added to the reaction mixture. The solution is filtered and after the addition of 77 ml of acetone cooled to approximately 20° C. The precipitated product was filtered and washed with acetone then dried at 50° C. under reduced pressure.

Workup

temperatureunder heating
filtrationThe solution is filtered
additionafter the addition of 77 ml of acetone
filtrationThe precipitated product was filtered
washwashed with acetone
customthen dried at 50° C. under reduced pressure

Sources & evidence

ORD record: ord-00932948f0fe4086aff20bd266b58d45
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006448B2

Reaction notes

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