Acetic Acid → 5-(3-(2-(7-Chloroquinolin-2-YL)ethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoic acid

HRID 22600Notes

Reaction equation

HRID 22600 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[S:21][CH2:22][CH2:23][C:24](O)=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[I-].Cl[C:35]1C=CC=[CH:37][N+:36]=1C.CNC.C(O)(=O)C>ClCCl.C(#N)C.C(N(CC)CC)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([CH:20]([S:21][CH2:22][CH2:23][C:24](=[O:25])[N:36]([CH3:37])[CH3:35])[S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 10413257HCID 10413257, compound

Product 1

HCID 199305215-(3-(2-(7-Chloroquinolin-2-YL)ethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoic acid

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of diacid (Example 25) (0.3 g) in dichloromethane (20 mL), acetonitrile (5 mL) and triethylamine (200 μL) was added 2-chloro-1-methylpyridinium iodide (180 mg). The mixture was stirred 30 min, cooled to 0° and 0.32 mL of a 2M solution of dimethylamine in toluene was added. The reaction was stirred 2 hours at room temperature. The reaction mixture was poured onto NH4OAc buffer and acetic acid (5 mL) was added. The mixture was extracted with ethyl acetate, which was dried over sodium sulfate and evaporated. Purification of the residue by flash chromatography starting with 15% and finishing with 30% of THF in toluene containing 1% of acetic acid afforded the title compound.

Workup

  1. temperaturecooled to 0°
  2. stirringThe reaction was stirred 2 hours at room temperature
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate, which
  5. dry with materialwas dried over sodium sulfate
  6. customevaporated
  7. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-6a7ee6954ddc497abbbbcc193478656f
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Reaction notes

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