Ethanolamine → HCID 57597227, compound

HRID 1925980Notes

Reaction equation

HRID 1925980 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[N:26]([CH2:27][C:28]4[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=4)[CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl.CN(C)CCCN=C=NCC.ON1C(=O)CCC1=O.[NH2:57][CH2:58][CH2:59][OH:60].C(=O)([O-])O.[Na+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[N:26]([CH2:27][C:28]4[CH:36]=[CH:35][C:31]([C:32]([NH:57][CH2:58][CH2:59][OH:60])=[O:33])=[CH:30][CH:29]=4)[CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

8

Reactant 5

HCID 700EthanolamineHCID 80170N-HydroxysuccinimideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57597378HCID 57597378, compound

Product 1

HCID 57597227HCID 57597227, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]methyl}benzoic acid (126 mg) in N,N-dimethylformamide (1.2 mL) were added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (72 mg) and 1-hydroxypyrrolidine-2,5-dione (43 mg), and the mixture was stirred at room temperature for 3 hrs. To this reaction mixture was added dropwise a solution of 2-aminoethanol (23 mg) in a mixed solvent of N,N-dimethylformamide (1.2 mL) and 10% aqueous sodium hydrogen carbonate (1.2 mL), and the mixture was stirred at room temperature for 48 hrs. The reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (25 mL×3). The organic layer was washed with saturated brine (25 mL×3), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (basic silica gel, eluent:ethyl acetate/methanol=10/0→8/2). The object fraction was concentrated under reduced pressure. Chloroform/diisopropyl ether (1/4) was added to the residue, and the resultant precipitate was collected by filtration and dried under reduced pressure to give the title compound (105 mg) as white powder crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 48 hrs
  2. extractionextracted with ethyl acetate (25 mL×3)
  3. washThe organic layer was washed with saturated brine (25 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. additionChloroform/diisopropyl ether (1/4) was added to the residue
  8. filtrationthe resultant precipitate was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-374fe5493a3e47c8b78df32a9211e50d
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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