Hydrochloric Acid → HCID 59244745, compound

HRID 912150Notes

Reaction equation

HRID 912150 reaction equation
OO.C[O:4][C:5](=[O:52])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[N:17]=[C:18]([N:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)[N:19]=[C:20]([C:21]4[CH:22]=[N:23][C:24]([N:27](CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)=[N:25][CH:26]=4)[C:15]=3[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.Cl.[OH-].[Na+:55]>O1CCCC1>[Na+:55].[NH2:27][C:24]1[N:23]=[CH:22][C:21]([C:20]2[C:15]3[CH2:14][CH2:13][N:12]([C:9]4[CH:8]=[CH:7][C:6]([C:5]([O-:52])=[O:4])=[CH:11][CH:10]=4)[C:16]=3[N:17]=[C:18]([N:46]3[CH2:47][CH2:48][O:49][CH2:50][CH2:51]3)[N:19]=2)=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 67385823HCID 67385823, compound

Product 1

HCID 59244745HCID 59244745, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Tetrahydrofuran/5M aqueous sodium hydroxide solution/30% hydrogen peroxide solution=4/2/1 solution of 4-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-benzoic acid methyl ester obtained in Example 1-D-08 was refluxed overnight, followed by neutralization with 6M hydrochloric acid. After filtering the precipitate, trifluoroacetic acid (1 ml) and concentrated sulfuric acid (2 drops) were added, followed by stirring at 40° C. for 4 hours. Concentration was carried out under reduced pressure, and water was added, followed by neutralization with 1M aqueous sodium hydroxide solution. After filtering the resulting solid, dichloromethane/hexane=9/1 was added, followed by stirring at room temperature for 30 minutes, to filter the solid. To this, 1M aqueous sodium hydroxide solution corresponding to 1 equivalent of sodium hydroxide was added, followed by stirring at room temperature for 10 minutes, and subsequently concentration was carried out under reduced pressure, to obtain the desired compound.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationAfter filtering the precipitate, trifluoroacetic acid (1 ml) and concentrated sulfuric acid (2 drops)
  3. additionwere added
  4. concentrationConcentration
  5. additionwas added
  6. filtrationAfter filtering the resulting solid, dichloromethane/hexane=9/1
  7. additionwas added
  8. stirringby stirring at room temperature for 30 minutes
  9. filtrationto filter the solid
  10. stirringby stirring at room temperature for 10 minutes
  11. concentrationsubsequently concentration

Sources & evidence

ORD record
ord-0d86646a54634f54bbcaf478bd1fa981
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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