Dimethyl Sulfoxide → HCID 59351217, compound

HRID 887450Notes

Reaction equation

Cl[C:2]1[C:3]([C:8]2([C:21]([O:23][CH3:24])=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][C:2]2[C:3]([C:8]3([C:21]([O:23][CH3:24])=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[N:4][CH:5]=[CH:6][N:7]=2)=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a vial with 1-tert-butyl 4-methyl 4-(3-chloropyrazin-2-yl)piperidine-1,4-dicarboxylate (58 mg, 0.163 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (39.5 mg, 0.163 mmol), and cesium carbonate (106 mg, 0.326 mmol) under N2 is added DMSO (1.0 mL). The reaction is heated to 100° C. in an oil bath 3 h. The reaction was cooled to rt, added to H2O (5 mL) and extracted with EtOAc (3×5 mL). The combined organic layers were dried (MgSO4) and concentrated. The residue was purified by RPHPLC to give 1-tert-butyl 4-methyl 4-(3-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1,4-dicarboxylate (36 mg, 0.064 mmol, 39.3% yield) as a white solid. [M+1]=562.1. IC50 (uM) +++++.

Workup

temperatureThe reaction was cooled to rt
extractionextracted with EtOAc (3×5 mL)
dry with materialThe combined organic layers were dried (MgSO4)
concentrationconcentrated
customThe residue was purified by RPHPLC

Sources & evidence

ORD record: ord-03801511608f485caf66e15ac2d643c3
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247418B2

Reaction notes

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