Thiazolidine → HCID 57657253, compound

HRID 244844Notes

Reaction equation

HRID 244844 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:22][CH2:23][C:24]([OH:26])=O)=[CH:5][C:4]=2[N:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[S:48]1[CH2:52][CH2:51][NH:50][CH2:49]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([CH3:17])([OH:19])[CH3:18])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:22][CH2:23][C:24](=[O:26])[N:50]3[CH2:51][CH2:52][S:48][CH2:49]3)=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 10444ThiazolidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69079561HCID 69079561, compound

Product 1

HCID 57657253HCID 57657253, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A round bottom flask, equipped with a stir bar, was charged with 3-[4-amino-2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoic acid (500 mg, 1.40 mmol), anhydrous pyridine (50 mL) and 1-hydroxybenzotriazole (379 mg, 2.80 mmol). After 30 minutes of stirring 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (537 mg, 2.80 mmol) was added to the reaction mixture in two portions. After 15 minutes, thiazolidine (250 mg, 2.80 mmol) was added in one portion. The pale yellow solution was stirred for 18 hours and then concentrated under reduced pressure. The resulting foam was dissolved in dichloromethane and washed with 1% aqueous sodium carbonate (2×15 mL). The combined aqueous fractions were extracted with chloroform (3×30 mL). The combined organic fractions were purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-25% gradient of CMA in chloroform) followed by recrystallization from acetonitrile to provide 516 mg of 1-{4-amino-2-ethyl-7-[3-oxo-3-(1,3-thiazolidin-3-yl)propyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as a white solid, mp 210-212° C.

Workup

  1. customA round bottom flask, equipped with a stir bar
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting foam was dissolved in dichloromethane
  4. washwashed with 1% aqueous sodium carbonate (2×15 mL)
  5. extractionThe combined aqueous fractions were extracted with chloroform (3×30 mL)
  6. customThe combined organic fractions were purified by chromatography
  7. washeluting with a 0-25% gradient of CMA in chloroform)
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-725dd6472b2d4ef9ab7f8d6d10091191
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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