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4-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazoline → HCID 10229547, compound

HRID 1371484
Notes
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Reaction equation

HRID 1371484 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Na].[Br:11][C:12]1[C:17]([NH2:18])=[C:16]2[O:19][CH2:20][O:21][C:15]2=[CH:14][CH:13]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][N:24]=1>CN(C=O)C.O>[Br:11][C:12]1[C:17]([NH:18][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][N:24]=2)=[C:16]2[O:19][CH2:20][O:21][C:15]2=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazolineHCID 219360135-Bromo-1,3-benzodioxol-4-amineHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 10229547HCID 10229547, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent
2×

Procedure

Sodium hexamethyldisilazane (1M solution in THF; 0.626 ml) was added to a solution of 6-bromo-2,3-methylenedioxyaniline (0.135 g) in DMF (2 ml) and the mixture was stirred at ambient temperature for 30 minutes. A solution of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (0.1 g) in DMF (3.5 ml) was added and the resultant mixture was stirred at ambient temperature for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (2×). The organic phase was washed with water and with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using an 80:17:3 mixture of methylene chloride, methanol and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.045 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.4 (m, 1H), 1.7 (m, 3H), 1.85 (m, 2H]), 2.3 (m, 2H), 2.95 (m, 2H), 3.25 (m, 2H), 3.55 (m, 2H), 4.05 (s, 3H), 4.3 (m, 2H), 6.15 (s, 2H), 7.05 (d, 1H), 7.3 (d, 1H), 7.4 (s, 1H), 8.15 (s, 1H), 8.9 (s, 1H); Mass Spectrum: M+H+ 515 and 517; Elemental Analysis: Found C, 55.74; H, 5.30; N, 10.76. C24H27BrN4O4 requires C, 55.93; H, 5.28; N, 10.87%.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe organic phase was washed with water and with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. additionan 80:17:3 mixture of methylene chloride, methanol

Sources & evidence

ORD record
ord-f1ad40cd42fe491b82201c54203cd3a9
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07157467B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes