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Trifluoroacetic acid → 6-(4-Hydroxy-3-methoxy-5-methylaminomethyl-phenyl)-4-(1H-indol-2-yl)-2H-pyridazin-3-one

HRID 2234141
ノート
印刷プレビュー

反応式

HRID 2234141 の反応式
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([CH2:29][NH:30][CH3:31])[C:26]([O:32]COCC[Si](C)(C)C)=[C:25]([O:41][CH3:42])[CH:24]=2)[N:20]=[N:19][C:18]=1[O:43]C)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:32][C:26]1[C:27]([CH2:29][NH:30][CH3:31])=[CH:28][C:23]([C:21]2[CH:22]=[C:17]([C:9]3[NH:8][C:16]4[C:11]([CH:10]=3)=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:18](=[O:43])[NH:19][N:20]=2)=[CH:24][C:25]=1[O:41][CH3:42]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 686384962-{3-Methoxy-6-[3-methoxy-5-methylaminomethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 1355131436-(4-Hydroxy-3-methoxy-5-methylaminomethyl-phenyl)-4-(1H-indol-2-yl)-2H-pyridazin-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
85 °C

実験手順

118 mg of 2-{3-Methoxy-6-[3-methoxy-5-methylaminomethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester is dissolved in 5 ml of dichloromethane and 5 ml of trifluoroacetic acid and the solution is stirred for 4 h at RT. The solvents are removed under reduced pressure. The residue is dissolved in 26 ml of acetonitrile and 117 mg of potassium iodide and 76 mg of chlorotrimethylsilane are added. The reaction is heated to 85° C. for 3 h. The reaction is quenched by the addition of a drop of water, the solvent is removed under reduced pressure and the product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 13 mg. LC-MS (ES+) 377 (M+H)+.

後処理

  1. customThe solvents are removed under reduced pressure
  2. dissolutionThe residue is dissolved in 26 ml of acetonitrile
  3. addition117 mg of potassium iodide and 76 mg of chlorotrimethylsilane are added
  4. customThe reaction is quenched by the addition of a drop of water
  5. customthe solvent is removed under reduced pressure
  6. customthe product is purified by preparative RP-HPLC
  7. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-03fa61cdec1b4e5e9a5c2ed3bb883f33
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709466B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート