Methanesulfonyl chloride → HCID 86627507, compound

HRID 1969982Notes

Reaction equation

HRID 1969982 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[NH:14][CH:15]=[CH:16][C:6]=3[C:5]=2[CH:4]=1.Cl.[CH2:18]([C:20]([OH:22])=[O:21])[CH3:19].NC1C=CC2NC(=O)C3NC=CC=3C=2C=1.C(C([O-])=O)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>>[CH3:43][S:44]([N:2]([CH3:1])[C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[NH:14][CH:15]=[CH:16][C:6]=3[C:5]=2[CH:4]=1)(=[O:46])=[O:45].[CH2:18]([C:20]([O-:22])=[O:21])[CH3:19]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 68940251HCID 68940251, compoundHCID 86627489HCID 86627489, compound

Product 1

HCID 86627507HCID 86627507, compoundYield 31%

Procedure

This compound is prepared according to synthesis 58, from 130 mg of 8-methylamino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate hydrochloride (synthesis 63) contaminated with 30% of 8-amino-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate to which 33 μL (0.42 mmol) of methanesulfonyl chloride is added. After purification by chromatography on silica (eluent dichloromethane/methanol/acetonitrile 94/3/3), 32 mg (31%) of 8-(methanesulfonyl-methyl-amino)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. additionis added
  3. customAfter purification by chromatography on silica (eluent dichloromethane/methanol/acetonitrile 94/3/3)

Sources & evidence

ORD record
ord-e70d4cdd37754665a5653487194b50d1
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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