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

HRID 634092Notes

Reaction equation

HRID 634092 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]=[N:37][CH:36]=[C:35]([N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]4[CH3:45])[N:34]=3)=[N:12][N:13]=2)=CC=1>C(O)(C(F)(F)F)=O>[CH3:45][CH:40]1[CH2:41][CH2:42][CH2:43][CH2:44][N:39]1[C:35]1[N:34]=[C:33]([C:17]2[C:16]3[C:20](=[CH:21][CH:22]=[C:14]([C:11]4[O:10][C:9]([NH2:8])=[N:13][N:12]=4)[CH:15]=3)[N:19]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=3)(=[O:24])=[O:25])[CH:18]=2)[CH:38]=[N:37][CH:36]=1

Participants

3

Reactant 1

HCID 68328232N-(4-methoxybenzyl)-5-(3-(6-(2-methylpiperidin-1-yl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 683280745-(3-(6-(2-methylpiperidin-1-yl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
120 °C

Procedure

N-(4-Methoxybenzyl)-5-(3-(6-(2-methylpiperidin-1-yl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (177 mg, 0.272 mmol) was weighed into a 5 mL glass microwave tube. The material was dissolved in TFA (1.5 mL) (Aldrich). The tube was sealed and the solution was heated at 120° C. for 10 min in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden). The excess TFA was removed in vacuo, the crude residue was treated with 1N NaOH and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The material was used in the next step without purification. MS (ESI, pos. ion) m/z 530.0 (M+1).

Workup

  1. customThe tube was sealed
  2. customThe excess TFA was removed in vacuo
  3. additionthe crude residue was treated with 1N NaOH
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe material was used in the next step without purification

Sources & evidence

ORD record
ord-b066b3bfa280404da0b6d322dcfc61af
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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