Diisopropylcarbodiimide → 4-({2-[5-Chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)-2-fluorobenzoic acid

HRID 56980

Reaction equation

HRID 56980 reaction equation
C(N=C=NC(C)C)(C)C.[Cl:10][C:11]1[C:12]([C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=2[C:30]#[N:31])=[CH:13][C:14](=[O:22])[N:15]([CH:17]([CH3:21])[C:18]([OH:20])=O)[CH:16]=1.[NH2:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([F:42])[CH:34]=1>ClC(Cl)C>[Cl:10][C:11]1[C:12]([C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=2[C:30]#[N:31])=[CH:13][C:14](=[O:22])[N:15]([CH:17]([CH3:21])[C:18]([NH:32][C:33]2[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([F:42])[CH:34]=2)=[O:20])[CH:16]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 3026804-Amino-2-fluorobenzoic acidHCID 1176225492-[5-Chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acid

Product 1

HCID 1176228314-({2-[5-Chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoyl}amino)-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Under argon and at RT, 37 mg (0.30 mmol, 1.0 eq.) of N,N′-diisopropylcarbodiimide were added to a solution of 100 mg (0.30 mmol) of 2-[5-chloro-4-(5-chloro-2-cyanophenyl)-2-oxopyridin-1(2H)-yl]propanoic acid (racemate) (Example 12.1D) in 2 ml of dichloroethane, the mixture was stirred for 10 min, 46 mg (0.30 mmol) of 4-amino-2-fluorobenzoic acid were added and the mixture was stirred under reflux overnight. Subsequently, the reaction mixture was concentrated under reduced pressure and the crude product was purified by preparative HPLC (Reprosil C18, water/methanol gradient). Yield: 41 mg (29% of theory)

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux overnight
  3. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  4. customthe crude product was purified by preparative HPLC (Reprosil C18, water/methanol gradient)

Sources & evidence

ORD record
ord-c9c2dcbfee0b4bc0b394f923bc0eaf8b
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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