Water → 7,7-Dimethyl-5-(1-(6-(trifluoromethyl)benzo[D]thiazol-2-YL)piperidin-4-YL)-5H-pyrrolo[2,3-B]pyrazin-6(7H)-one

HRID 707398Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 7,7-dimethyl-5-(piperidin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one hydrochloride (Intermediate 78) (0.088 g, 0.311 mmol), 2-chloro-6-(trifluoromethyl)benzo[d]thiazole (0.089 g, 0.373 mmol), and potassium carbonate (0.172 g, 1.245 mmol) in DMSO (3 mL) was heated at 110° C. overnight. The reaction mixture was cooled, H2O was added, and the solid was collected, dried and purified by ISCO (35% EtOAc/Hexanes) to give the title compound (93.5 mg, 67%). MS (M+1): 448. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.27 (1 H, s), 8.03-8.18 (2 H, m), 7.52-7.68 (2 H, m), 4.51-4.68 (1 H, m), 4.23 (2 H, d, J=12.5 Hz), 3.36-3.49 (2 H, m), 2.52-2.61 (2 H, m), 1.86 (2 H, d, J=10.4 Hz), 1.33 (6 H, s).

Workup

temperatureThe reaction mixture was cooled
customthe solid was collected
customdried
custompurified by ISCO (35% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-6c8ba8d9ccd148d7a3e661c655f077dc
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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