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

HRID 56980

반응식

HRID 56980 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-c9c2dcbfee0b4bc0b394f923bc0eaf8b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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