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

HRID 634108Notes

Reaction equation

HRID 634108 reaction equation
COC1C=CC(C[NH:8][C:9]2[O:10][C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:18]=[C:17]4[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[N:34]=3)=[N:12][N:13]=2)=CC=1>C(Cl)(Cl)Cl.C(O)(C(F)(F)F)=O>[O:42]1[CH2:41][CH2:40][N:39]([C:35]2[N:34]=[C:33]([C:17]3[C:16]4[C:20](=[CH:21][CH:22]=[C:14]([C:11]5[O:10][C:9]([NH2:8])=[N:13][N:12]=5)[CH:15]=4)[N:19]([S:23]([C:26]4[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=4)(=[O:25])=[O:24])[CH:18]=3)[CH:38]=[CH:37][CH:36]=2)[CH2:44][CH2:43]1

Participants

4

Reactant 1

HCID 68328310N-(4-methoxybenzyl)-5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 683280925-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 44.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of N-(4-methoxybenzyl)-5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.21 g, 0.33 mmol) in CHCl3 (2 mL) and TFA (2 mL) was heated at 80° C. for 12 h. Then the reaction mass was evaporated to dryness and ice cold H2O (10 mL) was added and basified with saturated NaHCO3 solution to pH 8. A white colored solid precipitated out which was collected by filtration and dried under vacuum to give 5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.075 g, 44.1%). MS (ESI, pos. ion) m/z: 517 (M+1); 1H NMR (DMSO-d6, 400 MHz): δ ppm 8.94 (s, 1H), 8.51 (s, 1H), 8.14 (d, J=8.8 Hz, 1H), 7.99 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.8 Hz, 1H), 7.68-7.64 (m, 1H), 7.42-7.36 (m, 3H), 7.18 (s, 1H), 6.82 (d, J=8.8 Hz, 1H), 3.77-3.75 (m, 4H), 3.57-3.56 (m, 4H), 2.3 (s, 3H).

Workup

  1. customThen the reaction mass was evaporated to dryness and ice cold H2O (10 mL)
  2. additionwas added
  3. customA white colored solid precipitated out which
  4. filtrationwas collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ccb9ff5428b548898e6a2a84d69adc88
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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