1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → rac-[1-({[2,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

HRID 1486291Notes

Reaction equation

HRID 1486291 reaction equation
[CH3:1][C:2]1[C:17]([C:18]([OH:20])=O)=[C:5]2[CH:6]=[C:7]([CH3:16])[CH:8]=[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[N:4]2[N:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[C:42]([O:46][C:47](=[O:56])[NH:48][C:49]([CH3:55])([CH2:52][CH2:53][CH3:54])[CH2:50][NH2:51])([CH3:45])([CH3:44])[CH3:43].C(N(CC)C(C)C)(C)C>O1CCCC1>[C:42]([O:46][C:47](=[O:56])[NH:48][C:49]([CH3:55])([CH2:52][CH2:53][CH3:54])[CH2:50][NH:51][C:18]([C:17]1[C:2]([CH3:1])=[N:3][N:4]2[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])=[CH:8][C:7]([CH3:16])=[CH:6][C:5]=12)=[O:20])([CH3:45])([CH3:44])[CH3:43]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 84723920rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamateHCID 1178597002,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridine-3-carboxylic Acid

Product 1

HCID 121434556rac-[1-({[2,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 45 mg (0.163 mmol) of 2,5-dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridine-3-carboxylic acid from Example 8A in 3 ml of tetrahydrofuran was admixed with 30 mg (0.177 mmol) of 1-hydroxybenzotriazole and 30 mg (0.177 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. The resulting solution was stirred at room temperature for 15 min, and then 45.7 mg (0.212 mmol) of rac-(1-amino-2-methylpentan-2-yl)carbamic acid tert-butyl ester from Example 152A were added, followed by 0.85 ml (0.212 mmol) of N,N-diisopropylethylamine. The mixture was stirred at room temperature for a further 18 h. The solvent was drawn off under reduced pressure and the residue was partitioned between ethyl acetate (10 ml) and water (10 ml). The organic phase was removed and washed with water and aqueous sodium chloride solution, dried with a phase separation cartridge and dried further under reduced pressure, which gave 80 mg (61% of theory, 54% pure) of the target compound.

Workup

  1. stirringThe mixture was stirred at room temperature for a further 18 h
  2. customthe residue was partitioned between ethyl acetate (10 ml) and water (10 ml)
  3. customThe organic phase was removed
  4. washwashed with water and aqueous sodium chloride solution
  5. customdried with a phase separation cartridge
  6. customdried further under reduced pressure, which
  7. customgave 80 mg (61% of theory, 54% pure) of the target compound

Sources & evidence

ORD record
ord-a6e579842a714d4690ce03a149ad595d
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

Loading…