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Diisopropylamine → 4-{3-[(4-{[5-Chloro-7-(pyridin-2-ylethynyl)-1,3-benzodioxol-4-yl]amino}-6-methoxyquinazolin-7-yl)oxy]propyl}-1-methylpiperazin-2-one

HRID 1785167
ノート
印刷プレビュー

反応式

HRID 1785167 の反応式
[Cl:1][C:2]1[CH:10]=[C:9](I)[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[C:31](=[O:36])[CH2:30]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1.[C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)#[CH:38].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:38]#[C:37][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[C:31](=[O:36])[CH2:30]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=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 137268EthynylpyridineHCID 688822194-[3-({4-[(5-Chloro-7-iodo-1,3-benzodioxol-4-yl)amino]-6-methoxyquinazolin-7-yl}oxy)propyl]-1-methylpiperazin-2-one

生成物 1

HCID 103262514-{3-[(4-{[5-Chloro-7-(pyridin-2-ylethynyl)-1,3-benzodioxol-4-yl]amino}-6-methoxyquinazolin-7-yl)oxy]propyl}-1-methylpiperazin-2-one収率 35%

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 4-[3-({4-[(5-chloro-7-iodo-1,3-benzodioxol-4-yl)amino]-6-methoxyquinazolin-7-yl}oxy)propyl]-1-methylpiperazin-2-one (0.17 g, 0.27 mmol), 2-ethynyl pyridine (0.056 g, 0.54 mmol) and diisopropylamine (0.075 ml, 0.54 mmol) in ethyl acetate (5 ml) was cooled to −20 C under a nitrogen atmosphere. To this was added copper (I) iodide (0.016 g, 0.081 mmol) and bis(triphenylphospine)palladium (II) chloride (0.038 g, 0.054 mmol). The reaction mixture was allowed to warm to ambient temperature and then stirred overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and 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 light brown solid (0.056 g, 35%). NMR Spectrum: (DMSOd6) 2.02 (m, 2H), 2.50 (t, 2H under DMSO), 2.72 (t, 2H), 2.84 (s, 3H), 3.01 (s, 2H), 3.28 (t, 2H under H2O), 3.94 (s, 3H), 4.20 (t, 2H), 6.23 (s, 2H), 7.21 (s, 1H), 7.32 (s, 1H), 7.45 (dd, 1H), 7.68 (d, 1H), 7.86 (m, 2H), 8.35 (s, 1H), 8.64 (d, 1H), 9.54 (s, 1H). Mass Spectrum: M+H+ 601 and M+H− 599.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. 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-94371dac08374875a89992117a0ddaef
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…

このページの内容参加物実験手順後処理出典と根拠反応ノート