Triethylamine → HCID 57576045, compound

HRID 1970038Notes

Reaction equation

HRID 1970038 reaction equation
C(N(CC)CC)C.O=C1C2NC=CC=2C2C=C(S(=O)(=O)NC3C=CC=CC=3)C=CC=2N1.C(C([O-])=O)C.[CH3:37][NH:38][CH2:39][C:40]([NH2:42])=[O:41].Cl[S:44]([C:47]1[CH:56]=[CH:55][C:54]2[NH:53][C:52](=[O:57])[C:51]3[NH:58][CH:59]=[C:60]([C:61]([OH:63])=[O:62])[C:50]=3[C:49]=2[CH:48]=1)(=[O:46])=[O:45]>ClCCl.CN(C)C=O>[C:40]([CH2:39][N:38]([CH3:37])[S:44]([C:47]1[CH:56]=[CH:55][C:54]2[NH:53][C:52](=[O:57])[C:51]3[NH:58][CH:59]=[C:60]([C:61]([OH:63])=[O:62])[C:50]=3[C:49]=2[CH:48]=1)(=[O:46])=[O:45])(=[O:41])[NH2:42]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151411N-MethylglycinamideHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acidHCID 86627536HCID 86627536, compound

Product 1

HCID 57576045HCID 57576045, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

584 μL (3 mmol) of triethylamine and 208 mg (1.68 mmol) of 2 methylamino-acetamide are added to 456 mg (1.4 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid suspended in 4 mL of anhydrous dichloromethane and 1 mL of anhydrous dimethylformamide. The reaction mixture is stirred for 3 days at room temperature. The solvents are evaporated then the residue is taken up in methanol. The solid is filtered, rinsed with methanol then diisopropyl ether and dried under vacuum to give 279 mg (53%) of 8-(carbamoylmethyl-methyl-sulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a white solid.

Workup

  1. customThe solvents are evaporated
  2. filtrationThe solid is filtered
  3. washrinsed with methanol
  4. dry with materialdiisopropyl ether and dried under vacuum

Sources & evidence

ORD record
ord-866892d9adfb424db90d404abfc5fec4
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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