rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamate → rac-[1-({[7-(Cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

HRID 1486288Notes

Reaction equation

HRID 1486288 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[N:14]3[N:15]=[C:16]([CH3:21])[C:17]([C:18]([OH:20])=O)=[C:13]3[CH:12]=[C:11]([CH3:22])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]([O:27][C:28](=[O:37])[NH:29][C:30]([CH3:36])([CH2:33][CH2:34][CH3:35])[CH2:31][NH2:32])([CH3:26])([CH3:25])[CH3:24]>S(Cl)(Cl)=O.ClCCl>[C:23]([O:27][C:28](=[O:37])[NH:29][C:30]([CH3:36])([CH2:33][CH2:34][CH3:35])[CH2:31][NH:32][C:18]([C:17]1[C:16]([CH3:21])=[N:15][N:14]2[C:9]([O:8][CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:10][C:11]([CH3:22])=[CH:12][C:13]=12)=[O:20])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 84723920rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamateHCID 1178597087-(Cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

Product 1

HCID 117864550rac-[1-({[7-(Cyclohexylmethoxy)-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 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 110 mg (0.364 mmol) of 7-(cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid from Example 120A in 1 ml of thionyl chloride was stirred at 100° C. for 1 h. After the reaction had ended, the solvent was drawn off under reduced pressure and the residue was suspended in 3 ml of dichloromethane and then added to a solution of 102.3 mg (0.473 mmol) of rac-(1-amino-2-methylpentan-2-yl)carbamic acid tert-butyl ester from Example 152A in 2 ml of dry dichloromethane. The resulting solution was stirred at room temperature overnight. The solvent was drawn off under reduced pressure and the residue was purified by flash chromatography using a prepacked silica gel cartridge (eluent:cyclohexane-ethyl acetate 10:1 to 1:1), which gave 40 mg (13% of theory, 59% pure) of the target compound.

Workup

  1. customthe residue was purified by flash chromatography
  2. customgave 40 mg (13% of theory, 59% pure) of the target compound

Sources & evidence

ORD record
ord-6059f380152948a3b9dac5e840eb4d2e
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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