Sodium Iodide → HCID 86601568, compound

HRID 1785185Notes

Reaction equation

HRID 1785185 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][O:14][CH3:15])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23](OCCCCl)=[CH:24][C:25]=2[O:27][CH:28]([CH3:30])[CH3:29])[N:20]=[CH:19][N:18]=1.C1(P([C:49]2[CH:54]=[CH:53]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:55]([N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)(=[O:57])[CH3:56].[I-].[Na+].C[O:67]CCO>ClCCl>[C:55]([N:58]1[CH2:63][CH2:62][N:61]([CH2:49][CH2:54][CH2:53][O:67][C:19]2[N:18]=[C:17]([NH:16][C:3]3[C:4]4[O:8][CH2:7][O:6][C:5]=4[C:9]([C:11]#[C:12][CH2:13][O:14][CH3:15])=[CH:10][C:2]=3[Cl:1])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[O:27][CH:28]([CH3:29])[CH3:30])[N:20]=2)[CH2:60][CH2:59]1)(=[O:57])[CH3:56]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 837951-AcetylpiperazineHCID 68882095HCID 68882095, compound

Product 1

HCID 86601568HCID 86601568, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-5-isopropoxyquinazolin-4-amine (0.253 g, as a 1:1.3 wt.:wt. mixture with triphenylphosphine) and N-acetyl piperazine (0.538 g) was dissolved in 2-methoxyethanol. Sodium iodide (0.031 g) was added and the reaction mixture was heated at 110° C. with stirring for 4 hours. The reaction mixture was cooled to room temperature, diluted with dichloromethane (150 ml), washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica using increasingly polar mixtures of methanol in dichloromethane as eluent. There was thus obtained the title compound (0.105 g) as a white foam; NMR Spectrum: (CDCl3) 1.53 (d, 6H), 2.03 (quin, 2H), 2.09 (s, 3H), 2.46 (m, 4H), 2.56 (t, 2H), 3.46 (s, 3H), 3.48 (t, 2H), 3.63 (t, 2H), 4.16 (t, 2H), 4.35 (s, 2H), 4.82 (sept, 1H), 6.10 (s, 2H), 6.49 (d, 1H), 6.83 (d, 1H), 7.06 (s, 1H), 8.51 (s, 1H), 9.41 (s, 1H); Mass Spectrum: M+H+ 610/612.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-6fba5396839f40eb94389fe8e81638ba
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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