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

HRID 634174Notes

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]CC6C=CC(OC)=CC=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>C(O)(C(F)(F)F)=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]([NH2:28])=[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: 120 °C

Procedure

A glass microwave reaction vessel was charged with 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (174 mg, 0.332 mmol) in TFA (1.0 ml). The reaction was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 30 min, then solvent was removed. The residue was purified with RP-HPLC to give 5-(3-(6-(4-chlorophenyl)pyridin-2-yl)-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (60.0 mg, 0.149 mmol, 44.7%) as an off-white solid. MS (ESI, pos. ion) m/z: 404 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.62 (1H, s), 8.90 (1H, s), 8.06-8.21 (3H, m), 7.70 (2H, d, J=4.1 Hz), 7.55-7.65 (2H, m), 7.50 (2H, d, J=8.4 Hz), 7.36 (1H, d, J=8.6 Hz), 7.16 (2H, s).

Workup

customA glass microwave reaction vessel
customsolvent was removed
customThe residue was purified with RP-HPLC

Sources & evidence

ORD record: ord-c22ece21d028447eb10896f03bbbd984
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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