Methanesulfonic Acid → HCID 131728801, compound

HRID 2079738Notes

Reaction equation

HRID 2079738 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH2:6]([O:12][C:13]([NH:15][N:16]=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH2:25][C:26]2[N:30]([CH3:31])[C:29]3[CH:32]=[CH:33][C:34]([C:36]([N:38]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=4)[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[O:37])=[CH:35][C:28]=3[N:27]=2)=[CH:20][CH:19]=1)=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C(OCC)(=O)C.C(O)C>[OH2:3].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH2:6]([O:12][C:13]([NH:15][N:16]=[CH:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][CH2:25][C:26]2[N:30]([CH3:31])[C:29]3[CH:32]=[CH:33][C:34]([C:36]([N:38]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=4)[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[O:37])=[CH:35][C:28]=3[N:27]=2)=[CH:22][CH:23]=1)=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:44]([O:43][C:41](=[O:42])[CH2:40][CH2:39][N:38]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1)[C:36]([C:34]1[CH:33]=[CH:32][C:29]2[N:30]([CH3:31])[C:26]([CH2:25][NH:24][C:21]3[CH:20]=[CH:19][C:18]([CH:17]=[N:16][NH:15][C:13]([O:12][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:14])=[CH:23][CH:22]=3)=[N:27][C:28]=2[CH:35]=1)=[O:37])[CH3:45].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 66706330HCID 66706330, compound

Product 1

HCID 131728801HCID 131728801, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1.53 g (15.93 mmol) of methanesulfonic acid in 15 mL of ethyl acetate was added dropwise to a solution of 10.0 g (15.93 mmol) of ethyl 3-[(2-{[4-(hexyloxycarbonylaminoiminomethyl)phenylamino]methyl}-1-methyl-1H-benzimidazole-5-carbonyl)pyridin-2-ylamino]propionate base (prepared as described in WO 98/37075) in 16.5 mL of 90% aqueous ethanol and 40 mL of ethyl acetate, with stirring, at 35° C. to 40° C. After a few minutes, the product began to crystallize out and was diluted with 30 mL of ethyl acetate. It was stirred for another 30 minutes at 35° C. to 40° C. and for a further 30 minutes at ambient (room) temperature, then the precipitate was suction filtered, washed with approximately 20 mL of ethyl acetate, and dried at 40° C. in the circulating air drying cupboard.

Workup

  1. waitAfter a few minutes
  2. customto crystallize out
  3. additionwas diluted with 30 mL of ethyl acetate
  4. stirringIt was stirred for another 30 minutes at 35° C. to 40° C. and for a further 30 minutes at ambient (room) temperature
  5. filtrationfiltered
  6. washwashed with approximately 20 mL of ethyl acetate
  7. customdried at 40° C. in the circulating air
  8. customdrying cupboard

Sources & evidence

ORD record
ord-c0358fa56bc44516a7ecbc658b26e0b1
Source dataset
uspto-grants-2011_04
Patent number
US07932273B2

Reaction notes

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