Triethylamine → HCID 13854272, compound

HRID 2292100Notes

Reaction equation

C(OC(Cl)=O)C(C)C.[N:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[NH2:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][C:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[NH:40][CH:39]=2)[CH2:32][CH2:31]1>C1COCC1>[NH:40]1[C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:38]([CH2:37][CH2:36][N:33]2[CH2:32][CH2:31][CH:30]([NH:29][C:19]([C:15]3[CH:14]=[C:13]4[C:18](=[CH:17][CH:16]=3)[N:9]=[CH:10][CH:11]=[CH:12]4)=[O:21])[CH2:35][CH2:34]2)=[CH:39]1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of isobutylchloroformate (0.65 g, 5.01 mmol) in dry THF (10 cm3) was added dropwise to a suspension of quinoline-6-carboxylic acid (0.87 g, 5.03 mmol) and triethylamine (0.6 g, 5.94 mmol) in dry THF (10 cm3) with stirring and cooling at -20° C. Stirring was continued while the temperature rose to ambient over 2 hours, then the mixture was cooled to -20° C. again and a solution of 3-[2-(4-amino-1-piperidyl)ethyl]indole (1.20 g, 4.94 mmol) in dry THF (20 cm3) was added dropwise. The mixture was stirred at room temperature overnight then evaporated to dryness and the residue triturated with water, aqueous potassium carbonate and water to give 1.4 g. of the title compound.

Workup

stirringStirring
temperaturethe mixture was cooled to -20° C. again
stirringThe mixture was stirred at room temperature overnight
customthen evaporated to dryness
customthe residue triturated with water, aqueous potassium carbonate and water
customto give 1.4 g

Sources & evidence

ORD record: ord-e433bd07823d4bb19b0d4468e0341ed3
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801595

Reaction notes

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