Hydrochloric Acid → HCID 21082693, compound

HRID 347430Notes

Reaction equation

HRID 347430 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]#[C:33][CH2:34][O:35][CH3:36])=[C:28]4[O:37][CH2:38][O:39][C:27]=34)=[C:18]([C:23]#[N:24])[CH:19]=[N:20]2)=[CH:15][C:14]=1[O:40][CH3:41].[I-].[Na+].[ClH:44]>C(OCC)(=O)C.C(OCC)C>[ClH:6].[ClH:44].[C:23]([C:18]1[CH:19]=[N:20][C:21]2[C:16]([C:17]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]#[C:33][CH2:34][O:35][CH3:36])=[C:28]3[O:37][CH2:38][O:39][C:27]=13)=[CH:15][C:14]([O:40][CH3:41])=[C:13]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:22]=2)#[N:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 31268PyrrolidineHCID 21082717HCID 21082717, compound

Product 1

HCID 21082693HCID 21082693, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyrrolidine (10 ml) was added to a mixture of 7-[2-(2-chloroethoxy)ethoxy]-3-cyano-6-methoxy-4-[4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyanilino]quinoline (0.225 g) and sodium iodide (0.133 g) and the reaction mixture was stirred at ambient temperature for 24 hours. The reaction mixture was evaporated and the residue was triturated under methylene chloride. The resultant solid was washed with water and dried. The material so obtained was dissolved in the minimum quantity of ethyl acetate and a solution of hydrogen chloride in diethyl ether (1M) was added. The resultant solid was isolated, washed with diethyl ether and dried. There was thus obtained the title compound as a solid (0.145 g); NMR Spectrum: (DMSOd6 and CD3CO2D at 100° C.) 1.84–1.89 (m, 4H), 3.29–3.39 (m, 9H), 3.88 (m, 2H), 3.94 (m, 2H), 3.96 (s, 3H), 4.3 (s, 2H), 4.36 (m, 2H), 6.04 (s, 2H), 6.84 (d, 1H), 6.94 (d, 1H), 7.46 (s, 1H), 7.87 (s, 1H), 8.56 (s, 1H); Mass Spectrum: M+H+ 545.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated under methylene chloride
  3. washThe resultant solid was washed with water
  4. customdried
  5. customThe material so obtained
  6. customThe resultant solid was isolated
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-c711cef9420e44998d55624830c34ac2
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Reaction notes

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