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Trifluoroacetic acid → 3-(4-methoxybenzyl)-9-(methylsulfanyl)-6,7-dihydro-3H-pyrazolo[4',3':5,6]pyrido[4,3-f]quinazoline

HRID 2383407
Notes
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Reaction equation

HRID 2383407 reaction equation
C[N:2](/[CH:4]=[C:5]1/[C:6](=O)[C:7]2[CH:8]=[N:9][C:10]([S:15][CH3:16])=[N:11][C:12]=2[CH2:13][CH2:14]/1)[CH3:3].[CH3:18][O:19][C:20]1[CH:32]=[CH:31][C:23]([CH2:24][N:25]2C(N)=[CH:28][CH:27]=[N:26]2)=[CH:22][CH:21]=1.FC(F)(F)C(O)=O>CO.C(O)(C)C>[CH3:18][O:19][C:20]1[CH:32]=[CH:31][C:23]([CH2:24][N:25]2[C:3]3[N:2]=[CH:4][C:5]4[CH2:14][CH2:13][C:12]5[N:11]=[C:10]([S:15][CH3:16])[N:9]=[CH:8][C:7]=5[C:6]=4[C:28]=3[CH:27]=[N:26]2)=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31612621-((4-methoxyphenyl)methyl)-1H-pyrazol-5-amineHCID 59490766(E)-6-((dimethylamino)methylene)-2-(methylthio)-7,8-dihydroquinazolin-5(6H)-one

Product 1

HCID 594904193-(4-methoxybenzyl)-9-(methylsulfanyl)-6,7-dihydro-3H-pyrazolo[4',3':5,6]pyrido[4,3-f]quinazolineYield 24.1%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of (E)-6-((dimethylamino)methylene)-2-(methylthio)-7,8-dihydroquinazolin-5(6H)-one (8 g, 32 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (7.2 g, 35 mmol) was added trifluoroacetic acid (3 mL). The reaction mixture was heated at 100° C. for 16 hours. The reaction was cooled to room temperature and diluted with a 1:1 mixture of methanol and isopropanol (40 mL). The mixture was stirred for 30 minutes and filtered. The solid obtained was then further purified using flash column chromatography (SiO2, gradient from 100% chloroform to 2% EtOAc in chloroform) to give the desired product (3.0 g, 24%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ 9.52 (s, 1H), 7.98 (s, 1H), 7.82 (s, 1H), 7.40 (d, J=8.0 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 5.64 (s, 2H), 3.78 (s, 3H), 3.16 (t, J=6.0 Hz, 2H), 3.10 (t, J=6.2 Hz, 2H), 2.65 (s, 3H); LCMS [M+H]: 390.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customThe solid obtained
  4. customwas then further purified

Sources & evidence

ORD record
ord-05dc7c4f22ba420ca333ca691a390dc6
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263610B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes