Water → HCID 66865103, compound

HRID 251869Notes

Reaction equation

HRID 251869 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([NH:23][CH2:24][CH:25](OCC)OCC)=[O:22].O.C(=O)([O-])O.[Na+]>C(O)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:25]=[CH:24][NH:23][C:21]1=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 59682862HCID 59682862, compound

Product 1

HCID 66865103HCID 66865103, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-3-(2,2-diethoxyethyl)urea (65 mg) was dissolved in formic acid (0.4 ml) and stirred at room temperature for 2 hours. Subsequently, the mixture was admixed with water and neutralized with saturated sodium hydrogencarbonate solution. After extracting three times with ethyl acetate, the combined organic phases were dried over magnesium sulfate, filtered, concentrated and purified by means of preparative chromatography. The fractions comprising product were combined, the acetonitrile was removed on a rotary evaporator, and the aqueous residue was neutralized with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. After the combined ethyl acetate phases had been dried over magnesium sulfate, they were filtered and concentrated to dryness. The residue was taken up with aqueous HCl and freeze-dried.

Workup

  1. extractionAfter extracting three times with ethyl acetate
  2. dry with materialthe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by means of preparative chromatography
  6. customthe acetonitrile was removed on a rotary evaporator
  7. extractionextracted three times with ethyl acetate
  8. dry with materialAfter the combined ethyl acetate phases had been dried over magnesium sulfate, they
  9. filtrationwere filtered
  10. concentrationconcentrated to dryness
  11. customfreeze-dried

Sources & evidence

ORD record
ord-9006b06bfaed49c1a0c55d3211744047
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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