Methanesulfonic Acid → HCID 58858026, compound

HRID 1162302Notes

Reaction equation

HRID 1162302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C@@H:12]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:30][C:29]4=[CH:31][N:32]=[C:33]([CH3:34])[N:28]4[C:27]3=[O:35])[CH2:22][CH2:21]2)=[O:19])[C:13]([CH3:17])([S:15][CH3:16])[CH3:14])=[O:10])=[CH:4][CH:3]=1.[CH3:36][S:37]([OH:40])(=O)=[O:38].ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH:11][C@@H:12]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:30][C:29]4=[CH:31][N:32]=[C:33]([CH3:34])[N:28]4[C:27]3=[O:35])[CH2:22][CH2:21]2)=[O:19])[C:13]([CH3:14])([S:15]([CH3:16])=[O:38])[CH3:17])=[O:10])=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([NH:11][C@@H:12]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:30][C:29]4=[CH:31][N:32]=[C:33]([CH3:34])[N:28]4[C:27]3=[O:35])[CH2:22][CH2:21]2)=[O:19])[C:13]([CH3:14])([S:37]([CH3:36])(=[O:40])=[O:38])[CH3:17])=[O:10])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 6395Methanesulfonic AcidHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58858016HCID 58858016, compound

Product 2

HCID 58858026HCID 58858026, compoundYield 22%HCID 68646826HCID 68646826, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N—(4-Chlorophenyl)—N′—((1S)-2-methyl-1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)-2-(methylthio)propyl)urea (0.52 g) obtained in Example 38 and methanesulfonic acid (0.06 ml) were dissolved in dichloromethane (20 ml). While the mixture was cooled to 0° C., 3-chloroperbenzoic acid (70%; 0.42 g) was added thereto, and mixed at 0° C. for 3 hours. To the reaction mixture was added an aqueous sodium sulfite solution, and mixed for 30 minutes. Then, an aqueous sodium hydrogen carbonate solution was added thereto, and the organic layer was collected by separation and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate/methanol=20/1 to 10/1) to obtain N—(4-chlorophenyl)—N′—((1S)-2-methyl-1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)-2-(methylsulfinyl)propyl)urea as colorless powder (0.12 g, 22%) and N—(4-chlorophenyl)—N′—((1S)-2-methyl-1-((4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)carbonyl)-2-(methylsulfonyl)propyl)urea as colorless powder (0.12 g, 22%).

Workup

  1. additionmixed at 0° C. for 3 hours
  2. additionmixed for 30 minutes
  3. customthe organic layer was collected by separation
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified with basic silica gel column (ethyl acetate/methanol=20/1 to 10/1)

Sources & evidence

ORD record
ord-d2bdfaf4b4cd4074b8d2264b990a37fb
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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