Methanesulfonic Acid → HCID 57153572, compound

HRID 1004520Notes

Reaction equation

HRID 1004520 reaction equation
C([O:3][C:4](=[O:33])[C@@H:5]([NH:23][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:6][NH:7][C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](OC(C)(C)C)=[O:17])[CH2:11]1)=[O:9])C.CS(O)(=O)=O.[C:39]([C:41]1[CH:49]=[CH:48][C:44](C(O)=O)=[CH:43][CH:42]=1)#[N:40].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(#N)C.O.C(N(CC)CC)C.CN(C=O)C>[C:39]([C:41]1[CH:49]=[CH:48][C:44]([C:16]([N:12]2[CH2:13][CH2:14][CH2:15][CH:10]([C:8]([NH:7][CH2:6][C@H:5]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:4]([OH:3])=[O:33])=[O:9])[CH2:11]2)=[O:17])=[CH:43][CH:42]=1)#[N:40]

Participants

10

Reactant 5

HCID 6395Methanesulfonic AcidHCID 120874-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57056368HCID 57056368, compound

Product 1

HCID 57153572HCID 57153572, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of the compound (373 mg) obtained in the above (1) in acetonitrile (1.5 ml) is added dropwise a solution of methanesulfonic acid (380 mg) in acetonitrile (1.5 ml), and the mixture is stirred at room temperature for 30 minutes. To the mixture are added dropwise DMF (4 ml) and triethylamine (400 mg) at 5-10° C. under ice-cooling, and further thereto are added 4-cyanobenzoic acid (129 mg), HOBT.H2O (146 mg) and then further WSC.HCl (183 mg). The mixture is stirred at 5-10° C. for 30 minutes, and further stirred at room temperature for 12 hours. The reaction mixture is poured into water, and extracted with ethyl acetate. The combined organic layers are washed successively with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and a saturated brine (each twice), and dried over magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (390 mg) as a white powder.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at 5-10° C. for 30 minutes
  3. stirringfurther stirred at room temperature for 12 hours
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers are washed successively with 1N hydrochloric acid
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution and a saturated brine (each twice), and dried over magnesium sulfate
  7. customThe desiccant is removed by filtration
  8. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d646bf5e65d74951b47e6f90da431e87
Source dataset
uspto-grants-2000_04
Patent number
US06048854

Reaction notes

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