Potassium Carbonate → HCID 59415759, compound

HRID 2061895Notes

Reaction equation

HRID 2061895 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH2:8].CN(C)/[CH:11]=[C:12](/[C:18](=[O:27])[C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:20]=1F)\[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>O>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:20]2[C:19](=[CH:24][C:23]([I:25])=[CH:22][CH:21]=2)[C:18](=[O:27])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4793071,2-Diaminocyclohexane, (+)-HCID 70809441(Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate2×

Product 1

HCID 59415759HCID 59415759, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

(1S,2S)-(+)-1,2-Diaminocyclohexane (500 mg, 4.3 mmol) was added to the solution of (Z)-ethyl-3-(dimethylamino)-2-(3-iodobenzoyl)acrylate (Intermediate 24, 0.34M, 11.7 mL, 3.9 mmol) and the mixture was heated at 50° C. for 3 h. The solvent was removed in vacuo and the residue was dried in a vacuum oven for 1.5 h. The residue was then dissolved in dimethyl formamide (7 mL) and potassium carbonate powder (753 mg, 5.5 mmol) was added. The reaction was heated at 70° C. for 3 h then cooled to room temperature. Water (30 mL) was added and the suspension was extracted with 1:1 ethyl acetate:methyl tert-butyl ether (3×50 mL). The organic layers were dried over sodium sulfate, and the solvent was removed in vacuo. The residue was suspended in methyl tert-butyl ether (20 mL) and stirred at 40° C. for 1 h. The suspension was filtered and the solid dried to give 724 mg (42% yield) of ethyl 1-((1S ,2S)-2-aminocyclohexyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate as a yellowish powder that was contaminated with about 40% bis dihydroquinoline. This material was used as is in the coupling step.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was dried in a vacuum oven for 1.5 h
  3. dissolutionThe residue was then dissolved in dimethyl formamide (7 mL)
  4. temperatureThe reaction was heated at 70° C. for 3 h
  5. temperaturethen cooled to room temperature
  6. extractionthe suspension was extracted with 1:1 ethyl acetate
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. customthe solvent was removed in vacuo
  9. filtrationThe suspension was filtered
  10. customthe solid dried

Sources & evidence

ORD record
ord-2d44291c0bec4d57ba95cf83f2bab1e6
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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