Water → 4-(6-(5-(5-(4-methoxybenzylamino)-1,3,4-thiadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrazin-2-yl)-1-methylpiperazin-2-one

HRID 634143Notes

Reaction equation

Cl[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]=[N:4][CH:3]=1.[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][C:44]1=[O:49].CCN(CC)CC.O>CN1C(=O)CCC1>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][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:36]=[CH:37][C:38]([CH3:39])=[CH:40][CH:41]=3)(=[O:34])=[O:33])[CH:9]=[C:8]4[C:6]3[N:7]=[C:2]([N:46]4[CH2:47][CH2:48][N:43]([CH3:42])[C:44](=[O:49])[CH2:45]4)[CH:3]=[N:4][CH:5]=3)=[N:18][N:19]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 155 °C

Procedure

To a solution of 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (100 mg, 0.166 mmol) in NMP (1 mL) was added 1-methylpiperazin-2-one (28.4 mg, 0.249 mmol) and Et3N (69.2 μL, 0.497 mmol). The reaction was stirred at 155° C. for 18 h, then cooled to RT. H2O was added and the resulting suspension was filtered to give the crude material. MS (ESI, pos. ion) m/z: 681 (M+1).

Workup

temperaturecooled to RT
filtrationthe resulting suspension was filtered

Sources & evidence

ORD record: ord-17b32183141d4e2bb48e1352e5131631
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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