Sodium Hydroxide → HCID 68157444, compound

HRID 243385Notes

Reaction equation

HRID 243385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C@@H:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3C2CCCCO2)[CH3:11])=[C:4]([NH:29][C:30]2[CH:35]=[N:34][CH:33]=[CH:32][N:31]=2)[CH:3]=1.[OH-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:9]([CH:10]([NH:12][C:13]3[N:21]=[CH:20][N:19]=[C:18]4[C:14]=3[NH:15][CH:16]=[N:17]4)[CH3:11])[N:29]([C:30]3[CH:35]=[N:34][CH:33]=[CH:32][N:31]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68157162HCID 68157162, compound

Product 1

HCID 68157444HCID 68157444, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

(S)—N-[4-Fluoro-2-(pyrazin-2-ylamino)phenyl]-2-[9-(tetrahydropyran-2-yl)-9H-purin-6-ylamino]propionamide (100 mg, 0.21 mmol) was dissolved in acetic acid (6.0 ml) and heated to 80° C. overnight. The reaction was cooled and neutralized with sodium hydroxide (1.0M aqueous) and the aqueous layer extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried over sodium sulfate and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-10% methanol in DCM) to yield 243 (30.0 mg, 39%). LCMS (Method C): RT 2.85 min [M+H]+ 376.0. 1H NMR (MeOD, 400 MHz): δ 8.94 (1H, s), 8.60 (2H, m), 7.98 (2H, s), 7.67 (1H, dd, J=8.7, 4.6 Hz), 7.10 (2H, m), 5.83 (1H, br s), 1.81 (3H, d, J=7.0 Hz)

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe aqueous layer extracted with EtOAc (×3)
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by chromatography (SiO2, 0-10% methanol in DCM)

Sources & evidence

ORD record
ord-7b323d344b1d4ae4ae41307504d8776f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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