Water → HCID 9874631, compound

HRID 843263Notes

Reaction equation

HRID 843263 reaction equation
[CH:1]1[C:6]([N:7]=[C:8]=[S:9])=[CH:5][C:4]2[C:10]([O:12][C:13]3([C:23]4[CH:24]=[CH:25][C:26]([OH:28])=[CH:27][C:22]=4[O:21][C:15]4[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]3=4)[C:3]=2[CH:2]=1)=[O:11].[NH2:29][C:30]1[C:39]2[N:40]=[C:41]([CH2:46][CH2:47][CH2:48][CH3:49])[N:42]([CH2:43][CH2:44][NH2:45])[C:38]=2[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N:31]=1.O>N1C=CC=CC=1>[NH2:29][C:30]1[C:39]2[N:40]=[C:41]([CH2:46][CH2:47][CH2:48][CH3:49])[N:42]([CH2:43][CH2:44][NH:45][C:8]([NH:7][C:6]3[CH:1]=[CH:2][C:3]([C:13]4[C:14]5[C:15]([O:21][C:22]6[C:23]=4[CH:24]=[CH:25][C:26](=[O:28])[CH:27]=6)=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=5)=[C:4]([CH:5]=3)[C:10]([OH:12])=[O:11])=[S:9])[C:38]=2[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18730Fluorescein 5-isothiocyanateHCID 22180889HCID 22180889, compound

Product 1

HCID 9874631HCID 9874631, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of fluorescein-5-isothiocyanate (778 mg, 2.0 mmol) in pyridine (5 mL) was added to a solution of 2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethaneamine (566 mg, 2.0 mmol) in pyridine (5 mL). The reaction mixture was heated at reflux for 30 minutes and then poured into water (50 mL). The resulting orange solid was isolated by filtration, dried under high vacuum and then recrystallized from pyridine to provide 0.76 g of the desired product as an orange solid, m.p. >245°. Analysis by high performance liquid chromatography indicated pure product. Analysis: Calculated for C37H32N6O5S: % C, 66.06; % H, 4.79; % N, 12.49; Found: % C, 63.03; % H, 4.89; % N, 12.59. High resolution mass spectroscopy: TM=673.2233 Da., MM=673.2251 Da.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 30 minutes
  3. customThe resulting orange solid was isolated by filtration
  4. customdried under high vacuum
  5. customrecrystallized from pyridine

Sources & evidence

ORD record
ord-6c6a1ab32ba944bcb3c0bf8038109da7
Source dataset
uspto-grants-2002_04
Patent number
US06376669B1

Reaction notes

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