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

HRID 705639노트

반응식

HRID 705639 반응식
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

참가 물질

8

반응물 1

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

생성물 1

HCID 136168658HCID 136168658, 화합물수율 96.1%

시약·촉매·용매 6

HCID 9942167Palladium hydroxide촉매HCID 176Acetic Acid용매HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5b7316a5b0144dcfa8822addc4749851
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174947B2

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