Sodium Hydroxide → HCID 68328053, compound

HRID 634119Notes

Reaction equation

HRID 634119 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:13]3=[N:14][C:15]([C:18]4[O:22][C:21]([NH2:23])=[N:20][N:19]=4)=[CH:16][CH:17]=[C:12]3[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=2)[CH:6]=[N:7][CH:8]=1.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:13]3=[N:14][C:15]([C:18]4[O:22][C:21]([NH2:23])=[N:20][N:19]=4)=[CH:16][CH:17]=[C:12]3[NH:11][CH:10]=2)[CH:6]=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68328059HCID 68328059, compound

Product 1

HCID 68328053HCID 68328053, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(3-(5-methoxypyridin-3-yl)-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-1,3,4-oxadiazol-2-amine (0.022 g, 0.048 mmol) and 1 M NaOH (aq.) (0.095 mL, 0.095 mmol) in 4 mL of EtOH was stirred overnight at RT. The reaction was then concentrated and the residue taken up in H2O and EtOAc. The EtOAc layer was put aside and the aqueous layer was acidified with 2 M HCl (aq.) and extracted with DCM and 3/1 CHCl3/i-PrOH (2×). The aqueous layer was concentrated to give an orange solid, which was washed with MeOH and the MeOH washes were dried over Na2SO4, filtered and concentrated to give an orange solid. The solid was triturated with DCM and the orange solid (20 mg) was collected by filtration. This material was purified by reverse phase HPLC (5-100% MeCN in H2O with 0.1% TFA) followed by silica gel chromatography (0-10% MeOH in DCM) to afford 5-(3-(5-methoxypyridin-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-1,3,4-oxadiazol-2-amine (0.0022 g, 7.14 μmol, 15.00%) as a white solid. MS (ESI, pos. ion) m/z: 309.0 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 4.01 (3H, s), 7.92-7.99 (2H, m), 8.11 (1H, d, J=2.93 Hz), 8.23 (1H, s), 8.43-8.47 (1H, m), 9.03 (1H, d, J=1.76 Hz).

Workup

  1. concentrationThe reaction was then concentrated
  2. extractionextracted with DCM and 3/1 CHCl3/i-PrOH (2×)
  3. concentrationThe aqueous layer was concentrated
  4. customto give an orange solid, which
  5. washwas washed with MeOH
  6. dry with materialthe MeOH washes were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an orange solid
  10. customThe solid was triturated with DCM
  11. filtrationthe orange solid (20 mg) was collected by filtration
  12. customThis material was purified by reverse phase HPLC (5-100% MeCN in H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-dfece084fd804ca88aaf8f04cc874ad6
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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