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Ethoxyacetyl chloride → 1-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol

HRID 2383152
ノート
印刷プレビュー

反応式

HRID 2383152 の反応式
C(OC1C=C2C(=CC=1)N=CC([N+]([O-])=O)=C2[Cl:22])C1C=CC=CC=1.C(OC1C=C2C(C(Cl)=C([N+]([O-])=O)C=N2)=CC=1)C1C=CC=CC=1.[CH2:45]([O:47][CH2:48][C:49](Cl)=[O:50])[CH3:46].[NH2:52][C:53]1[CH:54]=[N:55][C:56]2[C:61]([C:62]=1[NH:63][CH2:64][C:65]([CH3:68])([OH:67])[CH3:66])=[CH:60][C:59]([O:69][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)=[CH:58][CH:57]=2>C(#N)C>[NH2:52][C:53]1[CH:54]=[N:55][C:56]2[C:61]([C:62]=1[NH:63][CH2:64][C:65]([CH3:66])([OH:67])[CH3:68])=[CH:60][C:59]([O:69][CH2:70][C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[CH:58][CH:57]=2.[ClH:22].[CH2:70]([O:69][C:59]1[CH:60]=[C:61]2[C:56](=[CH:57][CH:58]=1)[N:55]=[CH:54][C:53]([NH:52][C:49](=[O:50])[CH2:48][O:47][CH2:45][CH3:46])=[C:62]2[NH:63][CH2:64][C:65]([OH:67])([CH3:66])[CH3:68])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=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 4

HCID 84189Ethoxyacetyl chlorideHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinolineHCID 670509451-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-olHCID 670509926-(Benzyloxy)-4-chloro-3-nitroquinoline

生成物 2

HCID 670509451-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol
HCID 67051090
N-{6-benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-ethoxyacetamide hydrochloride

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-{[3-Amino-6-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol was prepared according to the general methods described in Parts A and B of Example 54 using 6-benzyloxy-4-chloro-3-nitroquinoline in lieu of 7-benzyloxy-4-chloro-3-nitroquinoline in Part A. Ethoxyacetyl chloride (5.37 g, 43.8 mmol) was added to a solution of 1-{[3-amino-6-(benzyloxy)quinoline-4-yl]amino}-2-methylpropan-2-ol (7.45 g, 22.1 mmol) in acetonitrile (230 mL), and the reaction was stirred overnight. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane. The resulting solution was washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on a HORIZON HPFC system (an automated, modular high-performance flash purification product available from Biotage, Inc, Charlottesville, Va., USA) (silica gel cartridge, eluting with dichloromethane:methanol ranging in ratios from 98:2 to 95:5) to provide N-{6-benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-ethoxyacetamide hydrochloride.

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resulting solution was washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on a HORIZON HPFC system (
  8. custommodular high-performance flash purification product available from Biotage, Inc, Charlottesville, Va
  9. wash, USA) (silica gel cartridge, eluting with dichloromethane:methanol ranging in ratios from 98:2 to 95:5)

出典と根拠

ORDレコード
ord-3cf8d755e037415880daff93072d7c5a
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263594B2

反応ノート

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