Cesium carbonate → rac-{1-[({7-[(2,6-Difluoro-3-methoxybenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

HRID 1486292Notes

Reaction equation

HRID 1486292 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([CH3:28])([CH2:25][CH2:26][CH3:27])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:24])=[N:15][N:16]2[C:21]([OH:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:31][C:32]1[C:37]([F:38])=[C:36]([O:39][CH3:40])[CH:35]=[CH:34][C:33]=1[F:41].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.ClCCl>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([CH3:28])([CH2:25][CH2:26][CH3:27])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:24])=[N:15][N:16]2[C:21]([O:22][CH2:31][C:32]3[C:33]([F:41])=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[C:37]=3[F:38])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 834101602-(Chloromethyl)-1,3-difluoro-4-methoxybenzeneHCID 178444850HCID 178444850, compound

Product 1

HCID 117864681rac-{1-[({7-[(2,6-Difluoro-3-methoxybenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 80 mg (0.20 mmol) of rac-(1-{[(7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl)carbonyl]amino}-2-methylpentan-2-yl)carbamic acid tert-butyl ester from Example 141A and 38 mg (0.20 mmol) of 2-(chloromethyl)-1,3-difluoro-4-methoxybenzene from Example 133A in 2 ml of DMF was admixed with 129 mg (0.396 mmol) of caesium carbonate. The resulting suspension was stirred at RT for 72 h. The reaction mixture was diluted with dichloromethane (15 ml) and extracted with saturated aqueous sodium hydrogencarbonate solution (10 ml). The organic phase was concentrated under reduced pressure, which gave a crude material that contained the target compound in a multicomponent mixture (30% pure). The crude material was used in the next step without further purification.

Workup

  1. extractionextracted with saturated aqueous sodium hydrogencarbonate solution (10 ml)
  2. concentrationThe organic phase was concentrated under reduced pressure, which

Sources & evidence

ORD record
ord-a48a7f8e98e841cd884d2afe9e136f42
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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