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Triphenylphosphine → 4-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride

HRID 577374
ノート
印刷プレビュー

反応式

HRID 577374 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][CH2:33][CH:34]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]1.[Cl:41][C:42]1[CH:61]=[CH:60][C:45]([NH:46][C:47]2[C:56]3[C:51](=[CH:52][C:53](O)=[C:54]([O:57][CH3:58])[CH:55]=3)[N:50]=[CH:49][N:48]=2)=[C:44]([F:62])[CH:43]=1>C(Cl)Cl>[ClH:41].[Cl:41][C:42]1[CH:61]=[CH:60][C:45]([NH:46][C:47]2[C:56]3[C:51](=[CH:52][C:53]([O:32][CH2:33][CH:34]4[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]4)=[C:54]([O:57][CH3:58])[CH:55]=3)[N:50]=[CH:49][N:48]=2)=[C:44]([F:62])[CH:43]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776Triphenylphosphine2 回HCID 220568ethyl N-ethoxycarbonyliminocarbamate2 回HCID 2719711-Methyl-4-piperidinemethanol2 回HCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

生成物 1

HCID 231333204-(4-Chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride
収率 8.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triphenylphosphine (615 mg, 2.3 mmol) followed by diethyl azodicarboxylate (369 μl, 2.3 mmol) were added to a solution of 4-hydroxymethyl-1-methylpiperidine (151 mg, 1.1 mmol), (J. Med. Chem. 1973, 16, 156), and 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (250 mg, 0.78 mmol), (prepared as described for the starting material in Example 7), in methylene chloride (5 ml). After stirring for 30 minutes at ambient temperature, 4-hydroxymethyl-1-methylpiperidine (51 mg, 0.39 mmol), triphenylphosphine (102 mg, 0.39 mmol) and diethyl azodicarboxylate (61 μl, 0.39 mmol) were added. After stirring for 15 minutes, the volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methylene chloride/acetonitrile/methanol (70/10/20 followed by 75/5/20 and 80/0/20). The fractions containing the expected product were combined and the volatiles were removed by evaporation. The residue was dissolved in a mixture of methylene chloride and methanol and 5M hydrogen chloride in isopropanol was added. The suspension was concentrated and the solid was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline hydrochloride (16 mg, 4%).

後処理

  1. custom(prepared
  2. stirringAfter stirring for 15 minutes
  3. customthe volatiles were removed under vacuum
  4. customthe residue was purified by column chromatography
  5. washeluting with methylene chloride/acetonitrile/methanol (70/10/20 followed by 75/5/20 and 80/0/20)
  6. additionThe fractions containing the expected product
  7. customthe volatiles were removed by evaporation
  8. dissolutionThe residue was dissolved in a mixture of methylene chloride and methanol and 5M hydrogen chloride in isopropanol
  9. additionwas added
  10. concentrationThe suspension was concentrated
  11. filtrationthe solid was collected by filtration
  12. washwashed with ether
  13. customdried under vacuum

出典と根拠

ORDレコード
ord-018227f29e6540f9acb1920c84888081
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040548B2

反応ノート

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