Diisopropylamine → HCID 21082690, compound

HRID 347427Notes

Reaction equation

HRID 347427 reaction equation
C(NC(C)C)(C)C.[C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24](I)=[C:23]3[O:28][CH2:29][O:30][C:22]=13)=[CH:17][C:16]([O:31][CH3:32])=[C:15]([O:33][CH3:34])[CH:14]=2)#[N:9].[CH2:35]([CH:38]1[CH2:43][CH2:42][S:41](=[O:45])(=[O:44])[NH:40][CH2:39]1)[C:36]#[CH:37]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[C:8]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:37]#[C:36][CH2:35][CH:38]3[CH2:43][CH2:42][S:41](=[O:45])(=[O:44])[NH:40][CH2:39]3)=[C:23]3[O:28][CH2:29][O:30][C:22]=13)=[CH:17][C:16]([O:31][CH3:32])=[C:15]([O:33][CH3:34])[CH:14]=2)#[N:9]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 10310906HCID 10310906, compoundHCID 21082701HCID 21082701, compound

Product 1

HCID 21082690HCID 21082690, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

N,N-Diisopropylamine (0.043 g) was added to a stirred mixture of 3-cyano-4-(4-iodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline (0.2 g), 4-(2-propynyl)-1,1-dioxotetrahydro-4H-thiazine (0.145 g), bis(triphenylphosphine)palladium(II) dichloride (0.071 g), cuprous iodide (0.024 g) and ethyl acetate (10 ml) that had been cooled to −20° C. The resultant mixture was allowed to warm to ambient temperature and was stirred for 16 hours. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was washed with water and with a saturated brine solution, dried over magnesium sulphate and evaporated. The residue was triturated under a mixture of acetonitrile and water. The resultant solid was isolated and dried. There was thus obtained the title compound as a solid (0.05 g); NMR Spectrum: (DMSOd6) 2.97–3.04 (m, 4H), 3.12–3.18 (m, 4H), 3.72 (s, 2H), 3.83 (s, 3), 3.85 (s, 3H), 6.04 (s, 2H), 6.82 (d, 1H), 6.95 (d, 1H), 7.31 (s, 1H), 7.74 (s, 1H), 8.48 (s, 1H), 9.6 (s, 1H); Mass Spectrum: M+H+ 521.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with water and with a saturated brine solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated under a mixture of acetonitrile and water
  7. customThe resultant solid was isolated
  8. customdried

Sources & evidence

ORD record
ord-8db333b3fae24705901ec6825facd2e2
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Reaction notes

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