Sodium Hydroxide → HCID 16065084, compound

HRID 1991129Notes

Reaction equation

HRID 1991129 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:13]([C:14]3[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=3)=[CH:12][N:11](S(C3C=CC=CC=3)(=O)=O)[C:8]2=[N:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>CCO.CCOC(C)=O.[Cl-].[Na+].O>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:13]([C:14]3[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=3)=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59128695HCID 59128695, compound

Product 1

HCID 16065084HCID 16065084, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To crude azaindole 62 (118 mg) in EtOH (6 mL) was added 10% NaOH (1 mL) and the mixture was stirred in an oil bath (90° C.) for 4.5 h. The mixture was then cooled to r.t., diluted with AcOEt and saturated brine and partitioned. The aqueous layer was extracted with AcOEt (3×). The combined organic solutions were dried (MgSO4), filtered and concentrated. The residual yellow oil was partially purified by means of PTLC employing AcOEt as eluent to afford a semi-pure azaindole 63 (74 mg). A fraction (14 mg) of this material was further purified by means of preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give the desired azaindole 63 (5.6 mg, 25%); 1H NMR (400 MHz; CDCl3) δ 0.92 (s, 3H), 0.94 (s, 3H), 1.90 (m, 1H), 2.59 (d, J=7.2 Hz, 2H), 3.98 (s, 3H), 7.36 (d, J=2.1 Hz, 1H), 7.60 (s, 1H), 7.74 (d, J=0.6 Hz, 1H), 7.81 (d, J=1.8 Hz, 1H), 8.14 (d, J=1.8 Hz, 1H), 9.62 (br s, 1H); MS (CI) m/z 255 (MH+).

Workup

  1. temperatureThe mixture was then cooled to r.t.
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with AcOEt (3×)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residual yellow oil was partially purified by means of PTLC

Sources & evidence

ORD record
ord-69e6b97852a54b05882b230efc34be7c
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

Loading…