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

HRID 634103Notes

Reaction equation

HRID 634103 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[O:24][C:23]([NH:25]CC5C=CC(OC)=CC=5)=[N:22][N:21]=4)[CH:18]=3)[N:13]([S:35]([C:38]3[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[CH:12]=2)[N:6]=1)([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[O:24][C:23]([NH2:25])=[N:22][N:21]=4)[CH:18]=3)[N:13]([S:35]([C:38]3[CH:39]=[CH:40][C:41]([CH3:42])=[CH:43][CH:44]=3)(=[O:36])=[O:37])[CH:12]=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 683285465-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 683283115-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 85.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (220 mg, 0.36 mmol) in TFA (1.1 mL) was heated at 100° C. in a microwave for 30 min. The mixture was cooled to RT and TFA was removed in vacuo. The residue was washed with Et2O to give the crude material (150 mg, 85%). MS (ESI, pos. ion) m/z: 489.7 (M+1).

Workup

  1. customTFA was removed in vacuo
  2. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-25557207542f4c0f85caa1ae860be531
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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