HCID 66672661, compound → HCID 57639250, compound

HRID 2091652Notes

Reaction equation

HRID 2091652 reaction equation
[OH:1][C:2]1([C:31]([O:33]C)=[O:32])[CH2:7][CH2:6][CH:5]([N:8]2[C:16]([NH:17][C:18]3[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=3[F:26])=[N:15][C:14]3[C:9]2=[N:10][C:11]([NH:27][CH:28]([CH3:30])[CH3:29])=[N:12][CH:13]=3)[CH2:4][CH2:3]1>Cl>[OH:1][C:2]1([C:31]([OH:33])=[O:32])[CH2:7][CH2:6][CH:5]([N:8]2[C:16]([NH:17][C:18]3[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=3[F:26])=[N:15][C:14]3[C:9]2=[N:10][C:11]([NH:27][CH:28]([CH3:30])[CH3:29])=[N:12][CH:13]=3)[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 66672661HCID 66672661, compound

Product 1

HCID 57639250HCID 57639250, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 1-hydroxy-4-{2-[(methylethyl)amino]-8-[(2,4,6-trifluorophenyl)amino]purin-9-yl}cyclohexanecarboxylate (1.858 g, 3.858 mmol) was dissolved in 27 mL of 4.0 N aqueous hydrochloric acid solution. The reaction mixture was heated to 60° C. for 24 h. The mixture was then concentrated under reduced pressure to an oil and purified by preparative HPLC (20-80% acetonitrile-water, 0.1% TFA). The product was isolated as a white solid by filtration after evaporating acetonitrile from the combined fractions and neutralizing with concentrated ammonium hydroxide. (1.325 g, 73% yield).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure to an oil
  2. custompurified by preparative HPLC (20-80% acetonitrile-water, 0.1% TFA)
  3. customThe product was isolated as a white solid by filtration
  4. customafter evaporating acetonitrile from the combined fractions

Sources & evidence

ORD record
ord-deec7727521648e588f4086f63814209
Source dataset
uspto-grants-2013_05
Patent number
US08440661B2

Reaction notes

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