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p-Toluenesulfonic acid → 2-(4-(4-Isopropylpiperazin-1-yl)phenyl)-8-methoxyquinazolin-4(3H)-one

HRID 591651
Notes
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Reaction equation

HRID 591651 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:34][C:35]1[C:43]([O:44][CH3:45])=[CH:42][CH:41]=[CH:40][C:36]=1[C:37]([NH2:39])=[O:38]>CC(N(C)C)=O.O.C([O-])(O)=O.[Na+]>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]3[NH:39][C:37](=[O:38])[C:36]4[C:35](=[C:43]([O:44][CH3:45])[CH:42]=[CH:41][CH:40]=4)[N:34]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 20522144-(4-Isopropylpiperazin-1-yl)benzaldehydeHCID 185365712-Amino-3-methoxybenzamideHCID 23665763Sodium Bisulfite

Product 1

HCID 1359391202-(4-(4-Isopropylpiperazin-1-yl)phenyl)-8-methoxyquinazolin-4(3H)-oneYield 15.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 31374DimethylacetamideSolvent
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(4-isopropylpiperazin-1-yl)benzaldehyde (0.562 g, 2.40 mmol), NaHSO3 (0.310 g, 2.90 mmol), and p-TsOH (0.046 g, 0.24 mmol) was added to a solution of 2-amino-3-methoxybenzamide (0.400 g, 2.40 mmol) in DMA (15 mL). The reaction was stirred at 120° C. overnight. The mixture was diluted with H2O and saturated NaHCO3 and extracted with CH2Cl2. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with 0% to 10% MeOH/CH2Cl2 afforded the title compound (0.140 g, 15%). 1H NMR (300 MHz, DMSO-d6): δ 12.27 (s, 1H), 8.10 (d, J=8.9 Hz, 2H), 7.64-7.70 (m, 1H), 7.31-7.39 (m, 2H), 7.03 (d, J=9.1 Hz, 2H), 3.93 (s, 3H), 3.27-3.32 (m, 4H), 2.64-2.75 (m, 1H), 2.56-2.59 (m, 4H), 1.00 (d, J=6.6 Hz, 6H). ESI MS m/z 379 [M+H]+.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel eluting with 0% to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6e0a8c79472a44e3bd3b2a802f527031
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238640B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes