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Ethanol → 6,7-dimethoxy-2-(1-m-tolyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl)-3H-quinazolin-4-one

HRID 8724
Notes
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Reaction equation

HRID 8724 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[N:9]=[CH:8]2)[CH:2]=1.Cl[C:18]1[NH:27][C:26](=[O:28])[C:25]2[C:20](=[CH:21][C:22]([O:31][CH3:32])=[C:23]([O:29][CH3:30])[CH:24]=2)[N:19]=1.C(N(CC)CC)C.C(O)C>COC(O)C>[CH3:30][O:29][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:31][CH3:32])[N:19]=[C:18]([N:12]1[CH2:13][CH2:14][C:15]3[N:7]([C:3]4[CH:2]=[C:1]([CH3:16])[CH:6]=[CH:5][CH:4]=4)[CH:8]=[N:9][C:10]=3[CH2:11]1)[NH:27][C:26]2=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 219836441-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridineHCID 1354566642-Chloro-6,7-dimethoxy-3H-quinazolin-4-one

Product 1

HCID 1355325166,7-dimethoxy-2-(1-m-tolyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl)-3H-quinazolin-4-oneYield 56.9%

Reagents, catalysts & solvents

1
HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 18a (100 mg, 0.5 mmol), 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (100 mg, 0.4 mmol), and triethylamine (140 μL, 1.0 mmol) in 10 mL methoxyethanol was heated at 100° C. under nitrogen for 12 hr. The mixture was pumped to constant weight. The resulting residue was slurried with hot ethanol and allowed to reach ambient temperature. Vacuum filtration provided 95 mg of 6,7-dimethoxy-2-(1-m-tolyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl)-3H-quinazolin-4-one, 601, [M+H]+=418, as a white solid.

Workup

  1. customto reach ambient temperature
  2. filtrationVacuum filtration

Sources & evidence

ORD record
ord-2c8bf22c88d141f18e9c170291be32b9
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091200B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes