Cesium carbonate → HCID 70657492, compound

HRID 872849Notes

Reaction equation

HRID 872849 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C@@H:17]([NH:19][C:20]([C:22]3[CH:26]=[C:25]([C:27]([OH:30])([CH3:29])[CH3:28])[O:24][N:23]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6](F)[C:7]=1[C:8]#[N:9].[C:31](=O)([O-])[O-:32].[Cs+].[Cs+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C@@H:17]([NH:19][C:20]([C:22]3[CH:26]=[C:25]([C:27]([OH:30])([CH3:29])[CH3:28])[O:24][N:23]=3)=[O:21])[CH3:18])[N:12]=2)[CH:5]=[C:6]([O:32][CH3:31])[C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 67173614HCID 67173614, compound

Product 1

HCID 70657492HCID 70657492, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)—N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(2-hydroxypropan-2-yl)isoxazole-3-carboxamide (50 mg, 0.116 mmol), 5 ml of dry methanol and cesium carbonate (75 mg, 0.232 mmol) was reacted with stirring for 6 days keeping the temperature at 60° C. during the day and at RT during the night. The mixture was evaporated dissolved in DCM, extracted with water and dried. The product was purified by flash chromatography. Yield 60.3%. 1H-NMR (400 MHz; DMSO-d6): δ 1.15 (d, 3H), 1.46 (s, 6H), 4.01 (s, 3H), 4.32 (d, 2H), 4.40-4.51 (m, 1H), 5.68 (s, 1H), 6.49 (s, 1H), 7.00 (d, 1H), 7.54 (d, 1H), 7.67 (d, 1H), 7.83 (d, 1H), 8.75 (d, 1H).

Workup

  1. customwas reacted
  2. customat 60° C.
  3. customat RT
  4. customThe mixture was evaporated
  5. dissolutiondissolved in DCM
  6. extractionextracted with water
  7. customdried
  8. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-4ce03d1de9d44e4ba25f31142e31f7de
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…