HCID 20605084, compound → 8-hydroxy-5-[(1R)-1-hydroxy-2-[2-[4-(4-methoxy-3-phenylanilino)phenyl]ethylamino]ethyl]-1H-quinolin-2-one

HRID 1828875Notes

Reaction equation

HRID 1828875 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH:24][CH2:25][C@H:26]([OH:46])[C:27]4[CH:36]=[CH:35][C:34]([O:37]CC5C=CC=CC=5)=[C:33]5[C:28]=4[CH:29]=[CH:30][C:31](=[O:45])[NH:32]5)=[CH:18][CH:17]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>ClCCl.CO.[Pd]>[C:1]1([C:7]2[CH:8]=[C:9]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][NH:24][CH2:25][C@H:26]([OH:46])[C:27]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]5[C:28]=4[CH:29]=[CH:30][C:31](=[O:45])[NH:32]5)=[CH:20][CH:21]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 20605084HCID 20605084, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 98713868-hydroxy-5-[(1R)-1-hydroxy-2-[2-[4-(4-methoxy-3-phenylanilino)phenyl]ethylamino]ethyl]-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

The free base form of compound 1 was prepared from the protected intermediate PP. To a solution of N-{2-[4-(3-phenyl-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-hydroxy-2-(8-benzyloxy-2(1H)-quinolinon-5-yl)ethylamine (PP) prepared by the process of Examples 1 and 2 (43.0 g, 70 mmol) in 50% dichloromethane/methanol (200 mL) was added 20% palladium on carbon (8.6 g). The reaction was stirred vigorously under one atmosphere of hydrogen for 18 h. The solids were filtered off over Celite and washed with 50% dichloromethane/methanol (4×25 mL). The combined filtrates were evaporated to dryness to give compound 1 (38 g, purity 92% by HPLC ratio) as a gray solid.

Workup

  1. filtrationThe solids were filtered off over Celite
  2. washwashed with 50% dichloromethane/methanol (4×25 mL)
  3. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-23bb415a6952449f9121bc1c7e697dd3
Source dataset
uspto-grants-2006_06
Patent number
US07060712B2

Reaction notes

Loading…