Cyclopentylamine → HCID 25214730, compound

HRID 2382857Notes

Reaction equation

HRID 2382857 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=1.[CH:24]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25]1>C([O-])(O)=O.[Na+].CCOC(C)=O>[CH:24]1([NH:29][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=4)[N:10]=[C:6]3[CH:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 2906CyclopentylamineHCID 25212520HCID 25212520, compound

Product 1

HCID 25214730HCID 25214730, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-[5-chloro-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide ((B7), 50 mg; 0.14 mmol; 1.0 eq.) in cyclopentylamine (1.0 mL) was stirred at rt overnight. The reaction mixture was diluted with a saturated solution of NaHCO3 (10 mL) and EtOAc (5 mL). The two phases were separated and the organic phase was washed four times with a saturated solution of NaHCO3, after which the product precipitated in the organic phase. It was filtered, washed with a saturated solution of NaHCO3 and EtOAc, dried under vacuum and isolated as a white solid (13 mg, 23%). HPLC, Rt: 3.54 min. (purity 100%). LC/MS, M+(ESI): 391.3, M−(ESI): 389.3.

Workup

  1. customThe two phases were separated
  2. washthe organic phase was washed four times with a saturated solution of NaHCO3
  3. customafter which the product precipitated in the organic phase
  4. filtrationIt was filtered
  5. washwashed with a saturated solution of NaHCO3 and EtOAc
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0c1a69c242fa4345a5ee3e3bce098eeb
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

Loading…