Triethylamine → HCID 68936382, compound

HRID 1970016Notes

Reaction equation

HRID 1970016 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(CC)CC)C.[NH2:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1>>[C:39]([O:38][C:36]([N:33]1[CH2:34][CH2:35][CH:30]([NH:29][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])[CH2:31][CH2:32]1)=[O:37])([CH3:42])([CH3:40])[CH3:41]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 451210688-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 68936382HCID 68936382, compound

Procedure

8-(1-tert-Butoxycarbonyl-piperidin-4-ylsulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid is prepared according to synthesis 178, from 2.1 g (6.45 mmol) of 8-chlorosulfonyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid, 1.8 mL (12.9 mmol) of triethylamine and 1.29 g (6.45 mmol) of 4-amino-1-tert-butoxycarbonyl-piperidine to give, after purification by precipitation and trituration in water, 1.86 g (59%) of 8-(1-tert-butoxycarbonyl-piperidin-4-ylsulfamoyl)-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-87ca18d4911f46cf96284f4996c74a74
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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