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

Reaction equation

HRID 270709 reaction equation
[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

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-175525bb649c45499ac7b397c8d0d5a2
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Linked notes

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