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Dichloromethane → 6-Methoxy-4-(2,3-methylenedioxyanilino)-7-(3-methylsulphonylpropoxy)quinazoline monohydrochloride salt

HRID 1241572
ノート
印刷プレビュー

反応式

HRID 1241572 の反応式
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]4[O:31][CH2:32][O:33][C:26]=34)=[N:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:34][CH3:35].[CH3:36][S:37]([CH2:40][CH2:41][CH2:42]O)(=[O:39])=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)[Cl:64]>>[ClH:64].[CH3:35][O:34][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:14]=1[O:13][CH2:42][CH2:41][CH2:40][S:37]([CH3:36])(=[O:39])=[O:38])[N:21]=[CH:20][N:19]=[C:18]2[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]2[O:31][CH2:32][O:33][C:26]=12
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 5

HCID 6344DichloromethaneHCID 11776Triphenylphosphine2 回HCID 2004243-(Methylsulfonyl)-1-propanol2 回HCID 220568ethyl N-ethoxycarbonyliminocarbamate2 回HCID 1355941137-Hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline

生成物 1

HCID 21935989
6-Methoxy-4-(2,3-methylenedioxyanilino)-7-(3-methylsulphonylpropoxy)quinazoline monohydrochloride salt

実験手順

Diethyl azodicarboxylate (0.101 ml) was added dropwise to a stirred mixture of 7-hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline (0.1 g), 3-methylsulphonylpropan-1-ol (0.057 g), triphenylphosphine (0.168 g) and methylene chloride (5 ml) and the reaction mixture was stirred at ambient temperature. After a few minutes further portions of triphenylphosphine (0.084 g) and 3-methylsulphonylpropan-1-ol (0.022 g) were added followed by the dropwise addition of diethyl azodicarboxylate (0.050 ml). After another few minutes third portions of the same amounts of these reagents were added. The reaction mixture was evaporated and the residue was purified by column chromatography on silica using a 10:6:1 mixture of methylene chloride, ethyl acetate and methanol as eluent. The material so obtained was triturated under a 6M solution of hydrogen chloride in diethyl ether. There was thus obtained the title compound (0.108 g) as a white solid; NMR Spectrum: (DMSOd6 and CF3CO2D) 2.3 (m, 2H), 3.05 (s, 3H), 3.35 (m, 2H), 4.0 (s, 3H), 4.35 (t, 2H), 6.1 (s, 2H), 7.0 (m, 3H), 7.3 (s, 1H), 8.1 (s, 1H), 8.15 (s, 1H); Mass Spectrum: M+H+ 432.

後処理

  1. additionAfter another few minutes third portions of the same amounts of these reagents were added
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography on silica using
  4. additiona 10:6:1 mixture of methylene chloride, ethyl acetate and methanol as eluent
  5. customThe material so obtained
  6. customwas triturated under a 6M solution of hydrogen chloride in diethyl ether

出典と根拠

ORDレコード
ord-60106d64450d499dbb751b13a8b641b5
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07115615B2

反応ノート

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