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

HRID 634142Notes

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[S:21][C:20]([NH:22]CC5C=CC(OC)=CC=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>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[S:21][C:20]([NH2:22])=[N:19][N:18]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[N:4][CH:3]=1

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 (400 mg, 0.663 mmol) in TFA (1.5 mL). The mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 15 min, then cooled to RT. The solvent was removed in vacuo and the residue was diluted with p-dioxane (2 mL) and aq. NaOH (5 M, 0.8 mL) and the mixture was heated in a microwave at 100° C. for 15 min. The mixture was cooled to RT, diluted with water and extracted with CHCl3/iPrOH (4:1). The combined organic layers were dried, filtered and concentrated to give the crude material. MS (ESI, pos. ion) m/z: 329 (M+1).

Workup

customA glass microwave reaction vessel
temperaturecooled to RT
customThe solvent was removed in vacuo
additionthe residue was diluted with p-dioxane (2 mL) and aq. NaOH (5 M, 0.8 mL)
temperaturethe mixture was heated in a microwave at 100° C. for 15 min
temperatureThe mixture was cooled to RT
additiondiluted with water
extractionextracted with CHCl3/iPrOH (4:1)
customThe combined organic layers were dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-758fec79aa4a4d03b26b37a0f3aeb03c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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