HCID 59655836, compound → HCID 59655866, compound

HRID 2054369Notes

Reaction equation

HRID 2054369 reaction equation
[CH3:1][N:2]1[CH:10]=[N:9][C:8]2[C:7]([NH:11][CH:12]3[CH2:14][CH2:13]3)=[N:6][C:5]3=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[C:20]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])[CH:19]=4)=[N:17][N:4]3[C:3]1=2>C1COCC1.CO>[CH3:1][N:2]1[CH:10]=[N:9][C:8]2[C:7]([NH:11][CH:12]3[CH2:14][CH2:13]3)=[N:6][C:5]3=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[C:20]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:19]=4)=[N:17][N:4]3[C:3]1=2

Participants

3

Reactant 1

HCID 59655836HCID 59655836, compound

Product 1

HCID 59655866HCID 59655866, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 1-methyl-4-cyclopropylamino-7-(4′-fluoro-3′-methoxycarbonylethylphenyl)-pyrazolo[5,1-b]purine (57.4 mg, 0.141 mmol) in THF/MeOH/1.0 N NaOH (3.5 mL, 4:2:1) was stirred at room temperature. After 3 days, neutralization with 1.0 N HCl precipitated a white solid. Filtration followed by wash with H2O and acetone furnished the title compound (26.9 mg, 49%) as a white solid. 1H NMR (d-MeOD, 400 MHz): 7.88 (d, J=7.34 Hz, 1H), 7.83 (s, 1H), 7.86-7.80 (m, 1H), 7.12 (t, J=9.78 Hz, 1H), 6.58 (s, 1H), 4.32 (s, 3H), 3.01 (t, J=7.83 Hz, 2H), 2.90 (m, 1H), 2.65 (t, J=7.82 Hz, 2H), 0.93 (m, 2H), 0.70 (m, 2H).

Workup

  1. customneutralization with 1.0 N HCl precipitated a white solid
  2. filtrationFiltration
  3. washby wash with H2O and acetone

Sources & evidence

ORD record
ord-70da221db1034e7f86f85f6733794cda
Source dataset
uspto-grants-2008_02
Patent number
US07329668B2

Reaction notes

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