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Diisopropylamine → N-[5-chloro-7-({1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}ethynyl)-1,3-benzodioxol-4-yl]-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

HRID 1785166
ノート
印刷プレビュー

反応式

HRID 1785166 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[CH:12])[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1.I[C:37]1[N:41]([S:42]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)(=[O:44])=[O:43])[N:40]=[CH:39][CH:38]=1.C(NC(C)C)(C)C>C(OCC)(=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][C:37]2[N:41]([S:42]([C:45]3[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=3)(=[O:43])=[O:44])[N:40]=[CH:39][CH:38]=2)[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 7912DiisopropylamineHCID 159327945-iodo-1-tosyl-1H-pyrazoleHCID 86601565N-(5-chloro-7-ethynyl-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine

生成物 1

HCID 68883671N-[5-chloro-7-({1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}ethynyl)-1,3-benzodioxol-4-yl]-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine収率 51.3%

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒
HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-(5-chloro-7-ethynyl-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine (0.140 g, 0.28 mmol ), 5-iodo-1-[(4-methylphenyl)sulfonyl)-1H-pyrazole (0.147 g, 0.42 mmol) and diisopropylamine (0.078 ml, 0.56 mmol) in ethyl acetate (5 ml) was cooled to −20 C under a nitrogen atmosphere. To this mixture was added copper (I) iodide (0.016 g, 0.084 mmol) and bis(triphenylphospine)palladium (II) chloride (0.039 g, 0.056 mmol). The reaction mixture was allowed to warm to ambient temperature and then stirred overnight. The reaction mixture was filtered and then evaporated under reduced pressure. The residue was purified by flash chromatography on silica eluting with a mixture of 0-8% methanol in dichloromethane to give the product as a yellow solid (0.103 g, 51%). Mass Spectrum: M+H+ 717 and M+H− 715.

後処理

  1. filtrationThe reaction mixture was filtered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica eluting with a mixture of 0-8% methanol in dichloromethane

出典と根拠

ORDレコード
ord-040cac7a9c584dd08573d99a3cb4cd8a
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07504408B2

反応ノート

読み込み中…

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