Methanesulfonic Acid → 3-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid di-methanesulfonate

HRID 1877812Notes

Reaction equation

HRID 1877812 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH2:14][CH2:13]3)[C:9]3=[CH:25][C:26]([CH3:28])=[CH:27][N:8]3[CH2:7][C:6]=2[CH:29]=1.[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(#N)C>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([N:12]3[CH2:13][CH2:14][N:15]([CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH2:16][CH2:17]3)[C:9]3=[CH:25][C:26]([CH3:28])=[CH:27][N:8]3[CH2:7][C:6]=2[CH:29]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 601485641-Piperazinepropanoic acid, 4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)-alpha,alpha-dimethyl-

Product 1

HCID 866688493-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid di-methanesulfonateYield 96.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add acetonitrile (5 mL) to 3-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid (0.106 g, 0.255 mmol) to create a slurry. Add methanesulfonic acid (0.050 ml, 0.075 g, 0.76 mmol) to the stirring slurry (1000 rpm) and stir the resultant solution at 60° C. until a white solid precipitates. Cool this slurry, and isolate the solid by filtration to obtain 3-[4-(7-chloro-2-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid di-methanesulfonate (0.15 g).

Workup

  1. customprecipitates
  2. temperatureCool this slurry
  3. customisolate the solid
  4. filtrationby filtration

Sources & evidence

ORD record
ord-0482f4b9d6b147dcb4b460099dc6ba92
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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