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

HRID 634107Notes

Reaction equation

HRID 634107 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[O:21][C:20]([NH:22][CH2:23][C:24]5[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=5)=[N:19][N:18]=4)[CH:15]=3)[N:10]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:20]2[O:21][C:17]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[N:10]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:33])=[O:34])[CH:9]=[C:8]4[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[N:7]=3)=[N:18][N:19]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 867250945-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 68328310N-(4-methoxybenzyl)-5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 48%

Conditions

Temperature
130 °C

Procedure

The solution of 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (1.0 g, 1.70 mmol) and morpholine (0.178 g, 2.05 mmol) was taken in sealed tube and heated at 130° C. for 5 h, then cooled to RT and poured in cooled ice water (5 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried, filtered and concentrated to give N-(4-methoxybenzyl)-5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.52 g, 48%) as an off-white solid. MS (ESI, pos. ion) m/z: 637 (M+1); 1H NMR (DMSO-d6, 400 MHz): δ ppm 8.95 (s, 1H), 8.51 (s, 1H), 8.14 (d, J=8.8 Hz, 1H), 7.99 (d, J=8.4 Hz, 2H), 7.85-7.82 (m, 1H), 7.72-7.64 (m, 2H), 7.42-7.39 (m, 3H), 7.32 (d, J=8.4 Hz, 2H), 6.9 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 1H), 4.3 (s, 2H), 3.75 (m, 8H), 3.56 (s, 3H), 2.31 (s, 3H).

Workup

  1. temperaturecooled to RT
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bad12bcb16a4f9fb6d81c7df961d0eb
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

Loading…