Cesium carbonate → N-tert-Butyl-4-{[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}-2-methoxybenzamide

HRID 536555Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:14]3[CH2:16][CH2:15]3)[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][C:25]1[CH:37]=[CH:36][C:28]([C:29]([NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[C:27]([O:38][CH3:39])[CH:26]=1>CN(C=O)C>[C:32]([NH:31][C:29](=[O:30])[C:28]1[CH:36]=[CH:37][C:25]([CH2:24][N:11]2[C:10](=[O:13])[N:9]([CH:14]3[CH2:16][CH2:15]3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:12]2)=[CH:26][C:27]=1[O:38][CH3:39])([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 70 °C

Procedure

An amount of 70 mg (0.30 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one (preparation as per WO 2007/134862 Example 36A) was dissolved in 3 ml of DMF and admixed with 194 mg (0.59 mmol) of caesium carbonate and also 98 mg (0.33 mmol) of the compound from Example 23A. The mixture was stirred at 70° C. for 16 h. After cooling to RT, the crude mixture was freed from insoluble constituents by filtration and subjected directly to chromatographic purification [Method 8]. This gave 89 mg (66% of theory) of the target compound.

Workup

temperatureAfter cooling to RT
filtrationthe crude mixture was freed from insoluble constituents by filtration
customsubjected directly to chromatographic purification [Method 8]

Sources & evidence

ORD record: ord-c56725f519e94c0097fa4f39d61f594c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859601B2

Reaction notes

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