Triethylamine → 4-(6-(5-(5-(4-methoxybenzylamino)-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyridin-2-yl)-1-methylpiperidin-2-one

HRID 634169Notes

Reaction equation

F[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:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:42][N:43]1[CH2:48][CH2:47]N[CH2:45][C:44]1=[O:49].[CH3:50]CN(CC)CC>CN1C(=O)CCC1.C(Cl)Cl>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:20]2[S:21][C:17]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[N:10]([S:32]([C:35]3[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:9]=[C:8]4[C:6]3[N:7]=[C:2]([CH:50]4[CH2:47][CH2:48][N:43]([CH3:42])[C:44](=[O:49])[CH2:45]4)[CH:3]=[CH:4][CH:5]=3)=[N:18][N:19]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A glass microwave reaction vessel was charged with 5-(3-(6-fluoropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (300 mg, 0.512 mmol) and 1-methylpiperazin-2-one (117 mg, 1.024 mmol) in NMP (5 mL) followed by Et3N (214 μL, 1.537 mmol). The reaction was stirred and heated in an oil bath at 150° C. for 60 h, and the mixture was diluted with DCM and washed with H2O, brine, dried, filtered and concentrated to give the crude product. MS (ESI, pos. ion) m/z: 680 (M+1).

Workup

customA glass microwave reaction vessel
washwashed with H2O, brine
customdried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-8064e28098be4faa90dafe94d33479fd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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