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

HRID 56980

反応式

HRID 56980 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-c9c2dcbfee0b4bc0b394f923bc0eaf8b
出典データセット
uspto-grants-2016_09
特許番号
US09434690B2

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