Cesium carbonate → HCID 9909865, compound

HRID 2301340Notes

Reaction equation

HRID 2301340 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([O:11][CH2:12][C:13]2[N:14]([CH2:18]C)[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].CN1C(CO)=NC=N1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:4][C:2]([C:5]1[C:10]([O:11][CH2:12][C:13]2[N:14]([CH3:18])[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)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 9845621HCID 9845621, compoundHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanol

Product 1

HCID 9909865HCID 9909865, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To the product of Example 4 Step a) (2.67 g) and (2-methyl-2H-1,2,4-triazol-3-yl)methanol (prepared as described in EP-A-421210) (0.93 g) in dry dimethylsulfoxide (10 ml) was added caesium carbonate (3.14 g), and the mixture stirred at 50° C. under an atmosphere of dry nitrogen for 24 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 2.5% methanol-dichloromethane). The product was crystallised from ethyl acetate/diethyl ether/isohexane, to afford the title compound as a colourless solid. 1H NMR (500 MHz, DMSO-6) δ1.39 (9H, s), 3.74 (3H, s), 5.50 (2H, s), 7.46 (1H, m), 7.88 (1H, m), 7.90 (1H, s), 8.17 (1H, s); MS (ES+) m/z 418 [MH]+.

Workup

  1. temperatureOn cooling to room temperature
  2. customthe mixture was partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed with water
  5. customevaporated at reduced pressure
  6. customthe residue chromatographed on silica gel (eluent 2.5% methanol-dichloromethane)
  7. customThe product was crystallised from ethyl acetate/diethyl ether/isohexane

Sources & evidence

ORD record
ord-c83b14d6dc314947a035c09bf73fe38b
Source dataset
uspto-grants-2002_12
Patent number
US06500828B1

Reaction notes

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