Potassium Hydroxide → 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

HRID 634173Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]5[S:27][C:26]([NH:28][CH2:29][C:30]6[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=6)=[N:25][N:24]=5)[CH:21]=4)[N:16](S(C4C=CC(C)=CC=4)(=O)=O)[CH:15]=3)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]5[S:27][C:26]([NH:28][CH2:29][C:30]6[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=6)=[N:25][N:24]=5)[CH:21]=4)[NH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A glass microwave reaction vessel was charged with 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (225 mg, 0.332 mmol) in THF (5 mL) followed by KOH (1.5 mL, 1.50 mmol, 1 M). The mixture was heated in microwave at 80° C. for 90 min, then cooled to RT. The mixture was diluted with water and extracted with DCM. The combined organic layers were dried, filtered and concentrated to give the crude material. MS (ESI, pos. ion) m/z: 524 (M+1).

Workup

customA glass microwave reaction vessel
temperaturecooled to RT
extractionextracted with DCM
customThe combined organic layers were dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-404ca2763b4e470e92a9ab6ff8c8d5fb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

Loading…