Triethylamine → HCID 68933778, compound

HRID 1970018Notes

Reaction equation

HRID 1970018 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:8]=3[C:7]=2[CH:6]=1)(=[O:4])=[O:3].C([N:24]([CH2:27][CH3:28])[CH2:25]C)C.CNC1CCN([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])CC1>>[C:40]([O:39][C:37]([CH:5]1[CH2:14][CH2:28][CH:27]([N:24]([CH3:25])[S:2]([C:5]2[CH:14]=[CH:13][C:12]3[NH:11][C:10](=[O:15])[C:9]4[NH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:8]=4[C:7]=3[CH:6]=2)(=[O:4])=[O:3])[CH2:7][CH2:6]1)=[O:38])([CH3:41])([CH3:42])[CH3:43]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 68933778HCID 68933778, compound

Procedure

8-[(4-tert-Butoxycarbonyl-cyclohexyl)-methyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid is prepared according to synthesis 178, from 653 mg (2 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid, 334 mL (2.4 mmol) of triethylamine and 557 mg (2.6 mmol) of 4-methylamino-1-tert-butoxycarbonyl-piperidine to give, after purification by precipitation and trituration in water, 770 mg (76%) of 8-[(4-tert-butoxycarbonyl-cyclohexyl)-methyl-sulfamoyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid in the form of a beige solid.

Workup

  1. customto give
  2. customafter purification
  3. customby precipitation and trituration in water

Sources & evidence

ORD record
ord-1929d93de51f487787f729c3df7cc304
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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