Sodium Hydroxide → HCID 68328358, compound

HRID 634278Notes

Reaction equation

HRID 634278 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[N:24]=[C:23]([NH2:25])[O:22][N:21]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[N:24]=[C:23]([NH2:25])[O:22][N:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68328938HCID 68328938, compound

Product 1

HCID 68328358HCID 68328358, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (200 mg, 0.41 mmol) in 1,4-dioxane (2.0 mL) was added 10% aq NaOH (1.0 mL) and the reaction was heated at 100° C. for 2 h. The mixture was cooled to RT and treated with ice cold H2O (2.0 mL). The precipitate was collected through filtration and the crude product was purified with preparative HPLC (eluent: 10-60% AcCN in H2O with 0.01% TFA) to give 3-(3-(6-(isopropylamino)pyrazin-2-yl)-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (40 mg, 24.5%). MS (ESI, pos. ion) m/z: 336.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.96 (s, 1H), 9.07 (s, 1H), 8.25-8.22 (m, 2H), 7.76 (s, 2H), 7.72 (dd, J=6.8, 1.6 Hz, 1H), 7.64 (s, 1H), 7.54 (d, J=8.4 Hz, 1H), 4.30-4.27 (m, 1H), 1.32 (d, J=6.4 Hz, 6H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe precipitate was collected through filtration
  3. customthe crude product was purified with preparative HPLC (eluent: 10-60% AcCN in H2O with 0.01% TFA)

Sources & evidence

ORD record
ord-2ffc7c2d7880484bbef620289da74923
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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