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

HRID 634182Notes

Reaction equation

HRID 634182 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[O:23][C:22]([NH:24]CC6C=CC(OC)=CC=6)=[N:21][N:20]=5)[CH:17]=4)[N:12]([S:34]([C:37]4[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=4)(=[O:36])=[O:35])[CH:11]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[O:23][C:22]([NH2:24])=[N:21][N:20]=5)[CH:17]=4)[N:12]([S:34]([C:37]4[CH:38]=[CH:39][C:40]([CH3:41])=[CH:42][CH:43]=4)(=[O:36])=[O:35])[CH:11]=3)[CH:7]=[N:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 683280565-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 683288645-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 69%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

An orange-brown solution of 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (69.7 mg, 0.118 mmol) in TFA (0.5 mL) was heated at 120° C. (microwave for 10 min. TFA was removed in vacuo, and the resulting brown oil was partitioned between DCM (30 mL) and 0.5 N NaOH (10 mL). The organic layer was separated and concentrated onto silica gel. Chromatographic purification (silica gel, 0-100% EtOAc/Hex) furnished 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (38.3 mg, 0.081 mmol, 69%) as a white solid: MS (ESI, pos. ion) m/z: 473.1 (M+1).

Workup

  1. customTFA was removed in vacuo
  2. customthe resulting brown oil was partitioned between DCM (30 mL) and 0.5 N NaOH (10 mL)
  3. customThe organic layer was separated
  4. concentrationconcentrated onto silica gel
  5. customChromatographic purification (silica gel, 0-100% EtOAc/Hex)

Sources & evidence

ORD record
ord-fb26f5e514ea49ac8e8ea732aeb4e35f
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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