Water → HCID 86688549, compound

HRID 710553Notes

Reaction equation

HRID 710553 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2[S:18][C:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=3)=[CH:20][N:21]=2)=[O:15])[CH2:10][CH2:9]1.CCN=C=NCCCN(C)C.[CH3:42][S:43]([NH2:46])(=[O:45])=[O:44].O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:42][S:43]([NH:46][C:26]([C:25]1[CH:29]=[CH:30][C:22]([C:19]2[S:18][C:17]([NH:16][C:14]([N:11]3[CH2:12][CH2:13][C:8](=[CH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:9][CH2:10]3)=[O:15])=[N:21][CH:20]=2)=[CH:23][CH:24]=1)=[O:28])(=[O:45])=[O:44]

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 86688550HCID 86688550, compound

Product 1

HCID 86688549HCID 86688549, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

The compound (100 mg, 238 μmol) obtained in Example 20 was dissolved in DMF (4 mL), and N,N-dimethyl-4-aminopyridine (hereinafter referred to as DMAP) (6.0 mg, 48 μmol) and WSC (50 mg, 262 μmol) were added thereto, followed by stirring at room temperature for 10 minutes. Methanesulfonamide (34 mg, 357 μmol) was added to the resulting mixture, followed by stirring at room temperature for 16 hours. Water was added to the resulting mixture, and after extraction with methanol:chloroform (1:10), the extract was dried over anhydrous sodium sulfate. The desiccant was filtered off, and the residue obtained by evaporation under reduced pressure was purified using medium pressure flash column chromatography (silica gel; methanol:chloroform=1:15), thereby giving the title compound (15 mg, 13%) as a white solid.

Workup

  1. additionwere added
  2. stirringby stirring at room temperature for 16 hours
  3. extractionafter extraction with methanol:chloroform (1:10)
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified

Sources & evidence

ORD record
ord-93542c71f22747f6a67768239cd3a63a
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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