5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine → 5-(3-(6-morpholinopyridin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

HRID 634109Notes

Reaction equation

HRID 634109 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]5[O:26][C:25]([NH2:27])=[N:24][N:23]=5)[CH:20]=4)[N:15](S(C4C=CC(C)=CC=4)(=O)=O)[CH:14]=3)[CH:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1>[OH-].[K+].C1COCC1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[N:12]=[C:11]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]5[O:26][C:25]([NH2:27])=[N:24][N:23]=5)[CH:20]=4)[NH:15][CH:14]=3)[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 683280925-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 683280895-(3-(6-morpholinopyridin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 40.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14797Potassium HydroxideSolvent

Procedure

The solution of 5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.07 g, 0.135 mmol) in 10% KOH (0.7 mL) and THF (0.7 mL) was heated at 100° C. for 5 h. Then the reaction mass was evaporated to dryness and ice cold H2O (5 mL) was added and extracted with EtOAc. The combined organic layers were washed with brine, dried, filtered and concentrated. The crude product was recrystallized with 10% MeOH in CHCl3 to give 5-(3-(6-morpholinopyridin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.02 g, 40.8%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 363 (M+1); 1H NMR (DMSO-d6, 400 MHz): δ 11.74 (s, 1H), 8.91 (s, 1H), 8.11 (s, 1H), 7.64-7.52 (m, 3H), 7.19 (d, J=7.6 Hz, 1H), 7.04 (s, 2H), 6.65 (d, J=8.4 Hz, 1H), 3.79 (s, 4H), 3.58 (s, 4H).

Workup

  1. customThen the reaction mass was evaporated to dryness and ice cold H2O (5 mL)
  2. additionwas added
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystallized with 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-fb65023211c84d74b1c7ccff4b9015f9
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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