Tetrahydrofuran → HCID 51036303, compound

HRID 2403627Notes

Reaction equation

HRID 2403627 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19]2[N:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:32]([C:34](=[O:37])[CH2:35][NH2:36])[CH3:33])[CH:26]=3)=[CH:21][N:20]=2)[CH2:15][CH2:14]1)[C:7]([OH:9])=[O:8].C1COCC1.[OH-].[Na+]>O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19]2[N:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:32]([C:34](=[O:37])[CH2:35][NH2:36])[CH3:33])[CH:26]=3)=[CH:23][N:24]=2)[CH2:15][CH2:14]1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68107525HCID 68107525, compound

Product 1

HCID 51036303HCID 51036303, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3-chloro-4-{4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}benzoic acid dihydrochloride (3.0 g) were added THF (30 ml) and H2O (15 ml). To this mixture was added 1 N sodium hydroxide (10.6 ml), followed by stirring for 30 minutes. The precipitated solid was filtered and washed with water. The obtained product was dried at 50° C. under reduced pressure to obtain 3-chloro-4-{4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}benzoic acid (2.1 g) as a colorless solid.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customThe obtained product was dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-914f748dcc89455497b9903a9ba92351
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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