Sodium ethoxide → 5-(3-(6-ethoxypyrazin-2-yl)-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

HRID 634145Notes

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[S: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(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)[CH:5]=[N:4][CH:3]=1.[O-:42][CH2:43][CH3:44].[Na+]>CCO>[CH2:43]([O:42][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[S:21][C:20]([NH:22][CH2:23][C:24]5[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=5)=[N:19][N:18]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[N:4][CH:3]=1)[CH3:44]

Participants

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-thiadiazol-2-amine (90.0 mg, 0.149 mmol) and sodium ethoxide, 21 wt % solution in EtOH (0.152 mL, 0.448 mmol, Aldrich) in EtOH (1 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 1 h. Then the solvent was removed to give the crude material, which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 459 (M+1).

Workup

customA glass microwave reaction vessel
customThen the solvent was removed

Sources & evidence

ORD record: ord-2fdc210b7437475f96416af9f35c4bc3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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