N1-[3-Fluoro-4-[[6-methoxy-7-(phenylmethoxy)-4-quinolinyl]oxy]phenyl]-N2-(2-phenylethyl)ethanediamide → HCID 136168658、化合物

HRID 455834ノート

反応式

HRID 455834 の反応式
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:39])[C:28]([NH:30][CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:29])=[CH:22][C:21]=3[F:40])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:41][CH3:42])C1C=CC=CC=1>CO.CN(C=O)C.ClCCl.C(OCC)(=O)C.C(O)(=O)C.[OH-].[Pd+2].[OH-]>[F:40][C:21]1[CH:22]=[C:23]([NH:26][C:27](=[O:39])[C:28]([NH:30][CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:29])[CH:24]=[CH:25][C:20]=1[O:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:41][CH3:42])[CH:11]=2)[N:16]=[CH:15][CH:14]=1

参加物

8

反応物 1

HCID 57810393N1-[3-Fluoro-4-[[6-methoxy-7-(phenylmethoxy)-4-quinolinyl]oxy]phenyl]-N2-(2-phenylethyl)ethanediamide

生成物 1

HCID 136168658HCID 136168658、化合物収率 96.1%

試薬・触媒・溶媒 6

HCID 9942167Palladium hydroxide触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-{4-[(7-benzyloxy-6-methoxyquinolin-4-yl)oxy]-3-fluorophenyl}-N′-(2-phenylethyl)ethanediamide (32 g, 56 mmol) in methanol (200 mL), DMF (100 mL), dichloromethane (100 mL), ethyl acetate (100 mL) and acetic acid (5 mL) was added palladium hydroxide (4.2 g) and the mixture was shaken on a Parr hydrogenator under a hydrogen pressure of 45 psi for 4 h. The resulting suspension was filtered through celite and the solid residue was washed with boiling dichloromethane (2 L) and acetone (2 L). The combined filtrates were evaporated to yield N-{3-fluoro-4-[(7-hydroxy-6-methoxyquinolin-4-yl)oxy]phenyl}-N′-(2-phenylethyl)ethanediamide as an off-white solid (25.6 g, 95%). 1H NMR (400 MHz, d6-DMSO): δ 11.06 (s, 1H), 10.25 (br s, 1H), 9.12 (t, 1H), 8.40 (d, 1H), 8.01 (dd, 1H), 7.50-7.44 (m, 2H), 7.31-7.23 (m, 6H), 6.39 (d, 1H), 3.95 (s, 3H), 2.85 (t, 2H), 2.50 (m, 2H); IR (cm−1): 1666, 1624, 1585, 1520, 1481, 1427, 1377, 1256, 1211, 1194, 1022, 880, 850, 839, 802, 750, 700; LC/MS (M+H=476).

後処理

  1. filtrationThe resulting suspension was filtered through celite
  2. washthe solid residue was washed with boiling dichloromethane (2 L) and acetone (2 L)
  3. customThe combined filtrates were evaporated

出典と根拠

ORDレコード
ord-bf2ffedbe1a944ea9d01ba2f1ca0d660
出典データセット
uspto-grants-2013_07
特許番号
US08497284B2

反応ノート

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