Triethylamine → 6-Chloro-2-[(pyridin-2-ylmethyl)amino]nicotinoyl fluoride

HRID 1260582Notes

Reaction equation

HRID 1260582 reaction equation
C(N(CC)CC)C.[F:8]N1N=C(F)C=C(F)N1.[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[C:20]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[N:19]=1>ClCCl>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([F:8])=[O:23])=[C:20]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 216944332,4,6-Trifluoro-1,2,3-triazineHCID 551843576-Chloro-2-[(pyridin-2-ylmethyl)amino]nicotinic acid

Product 1

HCID 866423376-Chloro-2-[(pyridin-2-ylmethyl)amino]nicotinoyl fluorideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.27 ml of triethylamine (16.31 mmol) and 1.65 ml of 2,4,6-trifluorotriazine (19.57 mmol) are added successively to a suspension of 4.3 g of 6-chloro-2-[(pyridin-2-ylmethyl)amino]nicotinic acid (16.31 mmol) in 90 ml of dichloromethane. The mixture is stirred for 1 hour at ambient temperature and then a dichloromethane/ice-cold water mixture is added. The organic phase is washed 3 times with ice-cold NaHCO3aq and then dried over Na2SO4, filtered, and concentrated under vacuum. 3.97 g of expected product are obtained in the form of an orange solid. Yield=92%.

Workup

  1. washThe organic phase is washed 3 times with ice-cold NaHCO3aq
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cf8042ec4dda49ffa10943fbf59aed2b
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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