Cesium carbonate → HCID 57388889, compound

HRID 45795Notes

Reaction equation

Cl[CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[N:14]=[C:13]([S:17][CH3:18])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[C:6]([C:19]([NH2:21])=[O:20])=[N:5]1.CN1CCNCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[CH:3]([N:4]1[C:16]2[C:15]3[N:14]=[C:13]([S:17][CH3:18])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[C:6]([C:19]([NH2:21])=[O:20])=[N:5]1)=[CH2:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-chloroethyl)-8-(methylsulfanyl)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (50 mg 0.15 mmol) in methanol (3 ml), N-methylpiperazine (62 μl, 0.61 mmol) and cesium carbonate (97 mg, 0.3 mmol), were added. The resulting mixture was heated at 60° C. for 48 hours. The volatiles were removed under vacuum, the crude solid was dissolved with ethyl acetate and water, the organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude was purified by silica gel chromatography (DCM/EtOAc 8/2) to give the compound 1-ethenyl-8-(methylsulfanyl)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide as a yellow solid (15 mg 35% yield). LC/MS (254 nm) HPLC method 2 Rt 5.34 min. 1H NMR (401 MHz, DMSO-d6) δ 8.58 (s, 1H), 8.35 (dd, J=8.73, 15.44 Hz, 1H), 7.71 (s, 1H), 7.46 (br. s., 1H), 5.96 (d, J=15.38 Hz, 1H), 5.15 (d, J=8.67 Hz, 1H), 3.00-3.09 (m, 2H), 2.86-2.94 (m, 2H), 2.56 (s, 3H). HRMS (ESI) calcd for C13H13N5OS [M+H]+ 288.0914 found 288.0913.

Workup

customThe volatiles were removed under vacuum
dissolutionthe crude solid was dissolved with ethyl acetate and water
washthe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude was purified by silica gel chromatography (DCM/EtOAc 8/2)

Sources & evidence

ORD record: ord-fc0586d3271144f3980fc04f4a71e052
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541576B2

Reaction notes

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