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

HRID 634137Notes

Reaction equation

[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]5[S:24][C:23]([NH:25]CC6C=CC(OC)=CC=6)=[N:22][N:21]=5)[CH:18]=4)[N:13]([S:35]([C:38]4[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=4)(=[O:37])=[O:36])[CH:12]=3)[CH:8]=[N:7][CH:6]=2)[CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([C:20]5[S:24][C:23]([NH2:25])=[N:22][N:21]=5)[CH:18]=4)[N:13]([S:35]([C:38]4[CH:39]=[CH:40][C:41]([CH3:42])=[CH:43][CH:44]=4)(=[O:37])=[O:36])[CH:12]=3)[CH:8]=[N:7][CH:6]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

A glass microwave reaction vessel was charged with 5-(3-(6-(cyclopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (120 mg, 0.192 mmol) in TFA (1.5 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 120° C. for 15 min. Then the solvent was removed. The residue was diluted with DCM and washed with sat. NaHCO3, dried, filtered and concentrated to give the crude material, which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 504 (M+1).

Workup

customA glass microwave reaction vessel
customThen the solvent was removed
additionThe residue was diluted with DCM
washwashed with sat. NaHCO3
customdried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-dc8c6ab3a5ea4e01a871c1ebbdbbf0e0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

Loading…