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Sodium triacetoxyborohydride → N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-6-(5-((4-((dimethylphosphinoyl)-methyl)piperazin-1-yl)methyl)furan-2-yl)quinazolin-4-amine

HRID 877100
ノート
印刷プレビュー

反応式

HRID 877100 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]4[O:28][C:27]([CH:29]=O)=[CH:26][CH:25]=4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:9][C:8]=1[Cl:31].[CH3:35][P:36]([CH2:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)([CH3:38])=[O:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]4[O:28][C:27]([CH2:29][N:43]5[CH2:42][CH2:41][N:40]([CH2:39][P:36]([CH3:38])([CH3:35])=[O:37])[CH2:45][CH2:44]5)=[CH:26][CH:25]=4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[CH:9][C:8]=1[Cl:31]
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 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11181296(5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehydeHCID 203769071-[(Dimethylphosphoryl)methyl]piperazine

生成物 1

HCID 49856052N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-6-(5-((4-((dimethylphosphinoyl)-methyl)piperazin-1-yl)methyl)furan-2-yl)quinazolin-4-amine

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
触媒
HCID 6344Dichloromethane溶媒

実験手順

5-(4-(4-(3-fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)furan-2-carbaldehyde and 1-((dimethylphosphinoyl)methyl)piperazine were suspended in dichloromethane (20 mL). Sequentially, acetic acid (3 drops) and sodium triacetoxyborohydride (2 equiv.) were added at room temperature. The mixture was stirred at room temperature until the starting material disappeared. The reaction was quenched with 2N NaOH aqueous solution and extracted with dichloromethane. The combined organic layer and extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 20% methanol in dichloromethane to give the desired product as yellow crystalline solid. LCMS ESI(+) m/z: 635 (M+1). 1H NMR (300 MHz, CD3OD) δ 8.59 (s, 1H), 8.44 (s, 1H), 8.11 (m, 1H), 7.89 (m, 1H), 7.72 (m, 1H), 7.57 (m, 1H), 7.38 (m, 1H), 7.26 (m, 2H), 7.08 (m, 2H), 6.90 (d, 1H), 6.46 (d, 1H), 5.17 (s, 2H), 3.66 (s, 2H), 2.80 (m, 2H), 2.68 (m, 8H), 1.57 (d, 6H).

後処理

  1. customThe reaction was quenched with 2N NaOH aqueous solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layer and extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 20% methanol in dichloromethane

出典と根拠

ORDレコード
ord-eb6c0e9860404e2588045bccff14b069
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987284B2

反応ノート

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