Triethylamine → HCID 86013006, compound

HRID 2217807Notes

Reaction equation

HRID 2217807 reaction equation
[CH:1]1([CH2:7][C:8](Cl)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:21]=[CH:20][C:19]2[C:18]([NH2:22])=[C:17]([CH3:23])[CH:16]=[CH:15][C:14]=2[N:13]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[C:18]=2[NH:22][C:8](=[O:9])[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2757989Cyclohexylacetyl chlorideHCID 86009272HCID 86009272, compound

Product 1

HCID 86013006HCID 86013006, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclohexaneacetyl chloride (prepared according to the method of J. Am. Chem. Soc. 1986, 108,7686) (560 mg) in dichloromethane (5 mL) was added a mixture of 2-chloro-6-methyl-5-quinolinamine (prepared according to the method of Journal of the American Chemical Society 1947, 69, 179) (350 mg) and triethylamine (1 mL) in dichloromethane (5 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was poured into saturated sodium bicarbonate solution and extracted with dichloromethane (3×20 mL). The combined organic extracts were dried, filtered and evaporated to afford the sub-title compound (400 mg).

Workup

  1. customprepared
  2. customat 0° C
  3. extractionextracted with dichloromethane (3×20 mL)
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d36c30b426084202956245f6a150d896
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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