Ethanolamine → HCID 9951425, compound

HRID 362306Notes

Reaction equation

HRID 362306 reaction equation
[C:1]1([C:7]2[C:15]3[C:14]([NH2:16])=[N:13][CH:12]=[N:11][C:10]=3[N:9]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:38]([CH2:40][NH2:41])[OH:39]>CN(C=O)C>[OH:39][CH2:38][CH2:40][NH:41][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][CH:25]=[C:17]([N:9]2[C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:16])[C:15]=3[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8]2)[CH:18]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 54348204HCID 54348204, compound

Product 1

HCID 9951425HCID 9951425, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.0 g of 3-(5-phenyl-4-aminopyrrolo[2,3-d]pyrimidin-7-yl)benzoic acid (Example 15) is dissolved in 25 ml of warm DMF and the solution is cooled to 0° C. The mixture is treated with 0.54 g of carbonyldiimidazole and stirred at RT for 2 h. 0.19 g of ethanolamine is then added dropwise and the mixture is allowed to warm to RT and is stirred for 3 h. The mixture is then concentrated in an RE. The residue is dissolved in methylene chloride and the solution is crystallized overnight at 0° C. After filtration, the residue is dissolved in methylene chloride and chromatographed on silica gel (methylene chloride/methanol 15:1). The product-containing fractions are concentrated and the residue is taken up in a little methylene chloride and crystallized overnight at 0° C. The crystals formed are filtered off and dried under HV. N-(2-Hydroxyethyl)-3-(5-phenyl-4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-benzamide having a melting point of 194°-198° C. is obtained.

Workup

  1. temperatureto warm to RT
  2. stirringis stirred for 3 h
  3. concentrationThe mixture is then concentrated in an RE
  4. dissolutionThe residue is dissolved in methylene chloride
  5. customthe solution is crystallized overnight at 0° C
  6. filtrationAfter filtration
  7. dissolutionthe residue is dissolved in methylene chloride
  8. customchromatographed on silica gel (methylene chloride/methanol 15:1)
  9. concentrationThe product-containing fractions are concentrated
  10. customcrystallized overnight at 0° C
  11. customThe crystals formed
  12. filtrationare filtered off
  13. customdried under HV

Sources & evidence

ORD record
ord-404a5343e967471abd1a39a56e0e3857
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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