HCID 66602927, compound → HCID 23641323, compound

HRID 604171Notes

Reaction equation

HRID 604171 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:6][N:7]([CH2:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:23]=1[C:32]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[C:34]([C:40]([CH3:42])=[CH2:41])[N:33]=1)[C:8]1[N:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:10][N:9]=1)#[N:2]>CO.[C].[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH:43]=[C:44]([C:46]([F:47])([F:49])[F:48])[CH:45]=1)[CH2:6][N:7]([CH2:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:23]=1[C:32]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[C:34]([CH:40]([CH3:42])[CH3:41])[N:33]=1)[C:8]1[N:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:12][N:13]=1)#[N:2]

Participants

4

Reactant 1

HCID 66602927HCID 66602927, compound

Product 1

HCID 23641323HCID 23641323, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-(2-{(3-Cyano-5-trifluoromethyl-benzyl)-[2-(6-isopropenyl-3-methoxy-pyridin-2-yl)-4,5-dimethoxy-benzyl]-amino}-pyrimidin-5-yloxy)-butyric acid (24.5 mg) is dissolved in methanol (2 ml), and thereto is added 10% palladium-carbon (10 mg) and the mixture is stirred under hydrogen atmosphere at room temperature for 1 hour. The insoluble material is removed by filtration and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (chloroform:methanol=100:0→85:15) to give 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(6-isopropyl-3-methoxy-pyridin-2-yl)-4,5-dimethoxy-benzyl]-amino}-pyrimidin-5-yloxy)-butyric acid (21 mg). MS (m/z): 680 [M+H]+

Workup

  1. customThe insoluble material is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by silica gel column chromatography (chloroform:methanol=100:0→85:15)

Sources & evidence

ORD record
ord-7e42cc9516d942f3a8f6d7e724da3a42
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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