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Trifluoroacetic acid → 5-{[2-(Methylamino)ethyl]oxy}-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623789
ノート
印刷プレビュー

反応式

HRID 1623789 の反応式
[CH3:1][N:2]([CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([C:27]([NH:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[O:28])[CH:14]=1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][NH:2][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:15]([CH:14]=1)[C:27]([NH:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:28]
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

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 681081751,1-Dimethylethyl methyl[2-({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)ethyl]carbamate

生成物 1

HCID 699367815-{[2-(Methylamino)ethyl]oxy}-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
30 °C

実験手順

To the solution of 1,1-dimethylethyl methyl[2-({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)ethyl]carbamate (may be prepared as described in Description 75; 140 mg, 0.17 mmol) in dichloromethane (10 ml) was added trifluoroacetic acid (3.0 ml, 38.9 mmol) dropwise. After stirring at 30° C. for 2 h, the pH of the solution was adjusted to 7-8 by adding aqueous NaHCO3 solution. The mixture was extracted with dichloromethane. The dichloromethane layer was washed with brine, dried over Na2SO4, and concentrated to obtain a crude product. The crude product was purified by prep-HPLC (Gilson GX-281, waters X-Bridge 5 μm, 100*30 mm; A: 0.04% NH3.H2O/water, B: CH3CN; 0-6.0 min, 30%-55%; 6-12 min, 95%, RT=7.3 min) to yield the title compound as a white solid. 20 mg.

後処理

  1. extractionThe mixture was extracted with dichloromethane
  2. washThe dichloromethane layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThe crude product was purified by prep-HPLC (Gilson GX-281, waters X-Bridge 5 μm, 100*30 mm
  7. custom0-6.0 min, 30%-55%

出典と根拠

ORDレコード
ord-639af7fb18ec4474a8f7c8bc28f4ce95
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08778939B2

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