Cesium carbonate → HCID 18372417, compound

HRID 2301341Notes

Reaction equation

[CH3:1][C:2]([C:5]1[C:10]([O:11][CH2:12][C:13]2[N:14](CC)[N:15]=[CH:16][N:17]=2)=[N:9][N:8]2[C:20]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=3[F:31])=[N:21][N:22]=[C:7]2[CH:6]=1)([CH3:4])[CH3:3].[CH3:32]N1C=NC(CO)=N1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:3][C:2]([C:5]1[C:10]([O:11][CH2:12][C:13]2[N:17]=[CH:16][N:15]([CH3:32])[N:14]=2)=[N:9][N:8]2[C:20]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=3[F:31])=[N:21][N:22]=[C:7]2[CH:6]=1)([CH3:1])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To the product of Example 4 Step a) (0.559 g) and (1-methyl-1H-1,2,4-triazol-3-yl)methanol (prepared as described in EP-A-421210) (0.20 g) in dry dimethylsulfoxide (2 ml) was added caesium carbonate (0.67 g), and the mixture stirred at 60° C. under an atmosphere of dry nitrogen for 48 hours. On cooling to room temperature, the mixture was partitioned between ethyl acetate and water. The organic phase was separated, washed with water, evaporated at reduced pressure, and the residue chromatographed on silica gel (eluent 2% methanol-dichloromethane). The product was crystallised from ethyl acetate/diethyl ether, to afford the title compound as a colourless solid. 1H NMR (400 MHz, DMSO-d6) δ1.39 (9H, s), 3.85 (3H, s), 5.30 (2H, s), 7.46 (1H, m), 7.86 (1H, m), 8.14 (1H, s) 8.46 (1H, s); MS (ES+) m/z 418 [MH]+.

Workup

temperatureOn cooling to room temperature
customthe mixture was partitioned between ethyl acetate and water
customThe organic phase was separated
washwashed with water
customevaporated at reduced pressure
customthe residue chromatographed on silica gel (eluent 2% methanol-dichloromethane)
customThe product was crystallised from ethyl acetate/diethyl ether

Sources & evidence

ORD record: ord-20d3f70f091a4f60896f5eca030db64e
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500828B1

Reaction notes

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