Pyridine → 2-(Aminocyclopentyl)-6-chloronicotinic acid fluoride

HRID 1260593Notes

Reaction equation

HRID 1260593 reaction equation
N1C=CC=CC=1.[F:7]N1N=C(F)C=C(F)N1.[NH2:16][C:17]1([C:22]2[N:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=2[C:24](O)=[O:25])[CH2:21][CH2:20][CH2:19][CH2:18]1>ClCCl>[NH2:16][C:17]1([C:22]2[N:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=2[C:24]([F:7])=[O:25])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 216944332,4,6-Trifluoro-1,2,3-triazineHCID 866423392-(Aminocyclopentyl)-6-chloronicotinic acid

Product 1

HCID 875109342-(Aminocyclopentyl)-6-chloronicotinic acid fluorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.34 ml (4.15 mmol) of pyridine and 0.53 ml (6.23 mmol) of 2,4,6-trifluorotriazine are added to a suspension of 1.0 g (4.15 mmol) of 2-(aminocyclopentyl)-6-chloronicotinic acid in 12 ml of dichloromethane. The mixture is stirred for 2 hours at ambient temperature and then diluted with dichloromethane. The organic phase is washed twice with an ice-cold solution of NaHCO3aq and then dried over Na2SO4, filtered, and concentrated under reduced pressure. 1 g of product is obtained in the form of a brown oil, which is used immediately in the next step. Quantitative crude yield.

Workup

  1. washThe organic phase is washed twice with an ice-cold solution of NaHCO3aq
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b81df9a87a2a4268932e351d04814bfb
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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