Trifluoroacetic acid → 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

HRID 634099Notes

Reaction equation

HRID 634099 reaction equation
[Cl:1][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]CC5C=CC(OC)=CC=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]=[N:4][CH:3]=1.C(O)(C(F)(F)F)=O>>[Cl:1][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]([NH2:22])=[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]=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867250915-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Product 1

HCID 867250925-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amineYield 89%

Conditions

Temperature
120 °C

Procedure

A glass microwave reaction vessel was charged with 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (480 mg, 0.818 mmol) and TFA (2.0 mL). The mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 20 min then the solvent was removed. The crude residue was treated with 1N NaOH and the resulting precipitate was collected to give 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (340 mg, 0.728 mmol, 89%) as a light yellow amorphous solid. MS (ESI, pos. ion) m/z: 466.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.43 (1H, s), 9.01 (1H, s), 8.84 (1H, s), 8.71 (1H, s), 8.18 (1H, d, J=8.8 Hz), 8.03 (2H, m, J=8.4 Hz), 7.85-7.93 (1H, m), 7.45 (2H, m, J=8.2 Hz), 7.28 (2H, s), 2.34 (3H, s).

Workup

  1. customA glass microwave reaction vessel
  2. customthe solvent was removed
  3. additionThe crude residue was treated with 1N NaOH
  4. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-334820dfb50247e28d287cb4a78b93e6
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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