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Pyridine → N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide

HRID 1878039
ノート
印刷プレビュー

反応式

HRID 1878039 の反応式
[NH2:1][CH2:2][C:3]1([C:25]([F:28])([F:27])[F:26])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:13])[CH:11]=2)[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:5](=[O:23])[N:4]1[CH3:24].[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.Cl.CN(C)CCCN=C=NCC.[H-].ON1C2C=CC=CC=2N=N1.N1C=CC=CC=1>CN(C=O)C.O.C(Cl)(Cl)Cl>[Br:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:5](=[O:23])[N:4]([CH3:24])[C:3]2([CH2:2][NH:1][C:34](=[O:35])[C:33]1[CH:37]=[CH:38][C:30]([F:29])=[CH:31][CH:32]=1)[C:25]([F:27])([F:28])[F:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 1049PyridineHCID 99734-Fluorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 684871881-Hydroxybenzotriazole monohydrideHCID 684894644-(aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

生成物 1

HCID 68487482
N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

実験手順

4-(Aminomethyl)-6-bromo-1-(4-methoxybenzyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (36.8 mg, 0.080 mmol) was dissolved in DMF (1.0 mL), and 4-fluorobenzoic acid (28.1 mg, 0.201 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46.2 mg, 0.241 mmol), 1-hydroxybenzotriazole monohydride (36.9 mg, 0.241 mmol) and pyridine (0.032 mL, 0.402 mmol) were sequentially added to the reaction solution at room temperature. After the reaction solution was stirred overnight at room temperature, chloroform and water were added thereto and the mixture was stirred at room temperature. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by thin-layer chromatography (chloroform/methanol=1/10), whereby the objective N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide (33.9 mg, 73%) was obtained as a white solid.

後処理

  1. stirringthe mixture was stirred at room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter the drying agent was removed by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by thin-layer chromatography (chloroform/methanol=1/10), whereby the objective N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide (33.9 mg, 73%)
  8. customwas obtained as a white solid

出典と根拠

ORDレコード
ord-1dfc74c2f6d14c6587dedaa5cf478a4e
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08314094B2

反応ノート

読み込み中…

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