1-(3-Aminophenyl)ethanol → N-(2,4-dichloro-3-{2-[3-(1-hydroxy-ethyl)-phenylamino]-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}-phenyl)-3-trifluoromethyl-benzamide

HRID 270709

반응식

HRID 270709 반응식
[Cl:1][C:2]1[C:7]([C:8]2[C:21](=[O:22])[N:20]([CH3:23])[C:11]3[N:12]=[C:13](S(C)(=O)=O)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[C:6]([Cl:24])[CH:5]=[CH:4][C:3]=1[NH:25][C:26](=[O:37])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1.[OH:38][CH:39]([C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][CH:47]=1)[NH2:44])[CH3:40]>CCOC(C)=O>[Cl:1][C:2]1[C:7]([C:8]2[C:21](=[O:22])[N:20]([CH3:23])[C:11]3[N:12]=[C:13]([NH:44][C:43]4[CH:45]=[CH:46][CH:47]=[C:41]([CH:39]([OH:38])[CH3:40])[CH:42]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[C:6]([Cl:24])[CH:5]=[CH:4][C:3]=1[NH:25][C:26](=[O:37])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1

참가 물질

4

반응물 2

HCID 2224611-(3-Aminophenyl)ethanolHCID 59833791N-[2,4-dichloro-3-(2-methanesulfonyl-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide

생성물 1

HCID 11273621N-(2,4-dichloro-3-{2-[3-(1-hydroxy-ethyl)-phenylamino]-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}-phenyl)-3-trifluoromethyl-benzamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A mixture of N-[2,4-dichloro-3-(2-methanesulfonyl-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide (20 mg, 0.035 mmol) and 3-(1-hydroxyethyl)-aniline (50 mg, 0.364 mmol) is heated at 120° C. for ten minutes. The mixture is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by prep-HPLC to give N-(2,4-dichloro-3-{2-[3-(1-hydroxy-ethyl)-phenylamino]-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl}-phenyl)-3-trifluoromethyl-benzamide as a white solid. (17.9 mg, 81.4%). 1H NMR (CD3OD): δ 10.50 (s, 1H), 8.57 (d, 1H), 8.52 (s, 1H), 8.41 (s, 1H), 8.19 (s, 1H), 8.06 (d, 1H), 7.92 (s, 1H), 7.86 (d, 1H), 7.68 (t, 1H), 7.59 (d, 1H), 7.56 (s, 1H), 7.52 (d, 1H), 7.41 (t, 1H), 7.21 (s, 1H), 7.20 (d, 1H), 4.98 (q, 1H), 3.83 (s, 3H), 1.54 (d, 2H); MS m/z 629.10 (M+1).

후처리

  1. washwashed with saturated K2CO3, brine and water
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customis purified by prep-HPLC

출처 및 근거

ORD 기록
ord-175525bb649c45499ac7b397c8d0d5a2
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449582B2

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