Hydrochloric Acid → HCID 21082694, compound

HRID 347428Notes

Reaction equation

HRID 347428 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][O:28][CH3:29])=[C:21]4[O:30][CH2:31][O:32][C:20]=34)=[C:11]([C:16]#[N:17])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:33][CH3:34].FC(F)(F)C(O)=O.[F:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C(N(C(C)C)CC)(C)C.[I-].[Na+].[ClH:62]>C(Cl)Cl.C(OCC)C.COCCO>[ClH:1].[ClH:62].[C:16]([C:11]1[CH:12]=[N:13][C:14]2[C:9]([C:10]=1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][O:28][CH3:29])=[C:21]3[O:30][CH2:31][O:32][C:20]=13)=[CH:8][C:7]([O:33][CH3:34])=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:48]1[CH2:49][CH2:50][N:45]([CH2:44][CH2:43][F:42])[CH2:46][CH2:47]1)[CH:15]=2)#[N:17]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 21082719HCID 21082719, compoundHCID 85911586HCID 85911586, compound

Product 1

HCID 21082694HCID 21082694, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(3-chloropropoxy)-3-cyano-6-methoxy-4-[4-(3-methoxyprop-1-ynyl)-2,3-methylenedioxyanilino]quinoline (0.14 g), 1-(2-fluoroethyl)piperazine trifluoroacetic acid salt (0.158 g), diisopropylethylamine (0.189 g), sodium iodide (0.02 g) and 2-methoxyethanol (20 ml) was stirred and heated to 100° C. for 30 hours. The cooled mixture was evaporated and the resultant residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate and evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was dissolved in the minimum quantity of methylene chloride. The solution was diluted with diethyl ether 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 (0.045 g); NMR Spectrum: (DMSOd6 and CF3CO2D at 100° C.) 2.22–2.31 (m, 2H), 2.98–3.1 (m, 6H), 3.1.6–3.21 (m, 2H), 3.25–3.31 (m, 4H), 3.36 (s, 3H), 3.99 (s, 3H), 4.3–4.34 (m, 4H), 4.6 (t, 1H), 4.72 (t, 1H), 6.08 (s, 2H), 6.9 (d, 1H), 6.98 (d, 1H), 7.49 (s, 1H), 7.96 (s, 1H), 8.69 (s, 1H); Mass Spectrum: M+H+ 576.

Workup

  1. customThe cooled mixture was evaporated
  2. customthe resultant residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated
  5. customthe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  7. customThe material so obtained
  8. customThe resultant solid was isolated
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-116a59d0e2954ee9bbeac40a0e10823e
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Reaction notes

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