1,2-Dichloroethane → HCID 23557335, compound

HRID 1635897Notes

Reaction equation

HRID 1635897 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([C:14]([OH:16])=O)[C:11]([OH:13])=O)[CH3:2].[NH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2.[CH2:29](Cl)[CH2:30]Cl>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([C:11](=[O:13])[NH:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:30]2[C:29]=1[N:18]=[CH:19][CH:20]=[CH:21]2)[C:14](=[O:16])[NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2)[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 113598-AminoquinolineHCID 23557275HCID 23557275, compound

Product 1

HCID 23557335HCID 23557335, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Diacid 62 (150 mg, 0.609 mmol), 8-aminoquinoline (211 mg, 1.462 mmol), and DMAP (5 mg) were dissolved in THF (6 mL). To this solution was added EDC (350 mg, 1.827 mmol) and the reaction allowed to proceed overnight. The mixture was concentrated under reduced pressure and the product purified by flash chromatography (40% EtOAc/hexanes). Evaporation of the combined product fractions left 63 as a light brown solid (100 mg, 0.201 mmol, 14%). 1H-NMR (400 MHz, DMSO-d6) δ 10.85 (s, 2H), 8.92 (dd, 2H), 8.64 (dd, 2H), 8.40 (dd, 2H), 7.68 (dd, 2H), 7.62 (dd, 2H), 7.57 (t, 2H), 4.35 (t, 1H), 3.98 (q, 2H), 2.24 (t, 2H), 2.00 (m, 2H), 1.51 (m, 2H), 1.37 (m, 4H), 1.12 (t, 3H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe product purified by flash chromatography (40% EtOAc/hexanes)
  3. customEvaporation of the combined product fractions

Sources & evidence

ORD record
ord-78c946ef7a0843e990f8ed719661a305
Source dataset
uspto-grants-2003_01
Patent number
US06511990B1

Reaction notes

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