Dimethylamine → N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}-3,6-bis(dimethylamino)hexanamide

HRID 2416084Notes

Reaction equation

HRID 2416084 reaction equation
[CH2:1]([O:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:33][CH2:34][CH3:35])=[C:21]([NH:24][C:25](=[O:32])[CH:26]=[CH:27][CH2:28][CH2:29][CH2:30]Cl)[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:36]#[N:37])=[CH:11][C:10]=1[Cl:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].C[N:44]([CH3:47])[CH:45]=O.[CH3:48][NH:49][CH3:50]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:33][CH2:34][CH3:35])=[C:21]([NH:24][C:25](=[O:32])[CH2:26][CH:27]([N:49]([CH3:50])[CH3:48])[CH2:28][CH2:29][CH2:30][N:44]([CH3:47])[CH3:45])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:36]#[N:37])=[CH:11][C:10]=1[Cl:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 674Dimethylamine2×HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 69462615HCID 69462615, compound

Product 1

HCID 12148884N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}-3,6-bis(dimethylamino)hexanamide

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A stirred mixture of N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}6-chloro-2-hexenamide (0.58 g, 1.0 mmol), NaI (0.15 g, 1.0 mmol), tetrabutylammonium iodide (74 mg, 0.20 mmol), 4.0 ml of dimethylformamide, and 10 ml of 2.0 M dimethylamine in tetrahydrofuran was heated at 50° C. for 8 h. After the addition of 5 ml more 2.0 M dimethylamine in tetrahydrofuran the mixture was heated at 50° C. for an additional 8 h. After evaporation of the dimethylamine and tetrahydrofuran, the mixture was stirred in water, brought to pH˜9 with potassium carbonate, and filtered. The crude product was washed with water, dried, and chromatographed on silica gel with methylene chloride-ethyl acetate-methanol-triethylamine to give 464 mg of the title compound as an off-white solid; mass spectrum (electrospray, m/e) 628.9 (M+H)+, 315.1 (M+2H)+2.

Workup

  1. temperaturewas heated at 50° C. for an additional 8 h
  2. customAfter evaporation of the dimethylamine and tetrahydrofuran
  3. filtrationfiltered
  4. washThe crude product was washed with water
  5. customdried
  6. customchromatographed on silica gel with methylene chloride-ethyl acetate-methanol-triethylamine

Sources & evidence

ORD record
ord-cac6fe4f514548729ccf752edecd8529
Source dataset
uspto-grants-2004_11
Patent number
US06821988B2

Reaction notes

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