3,5-Pyridinedicarboxylic acid → 5-(Methyl-propylcarbamoyl)-nicotinic acid

HRID 732588

반응식

HRID 732588 반응식
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[C:3]([C:10]([OH:12])=[O:11])[CH:2]=1.C(N(C(C)C)CC)(C)C.C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:43][NH:44][CH2:45][CH2:46][CH3:47].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCl.CN(C=O)C>[CH3:43][N:44]([CH2:45][CH2:46][CH3:47])[C:7]([C:5]1[CH:6]=[N:1][CH:2]=[C:3]([CH:4]=1)[C:10]([OH:12])=[O:11])=[O:9]

참가 물질

8

반응물 5

HCID 103663,5-Pyridinedicarboxylic acidHCID 12315N-MethylpropylamineHCID 81531DiisopropylethylamineHCID 945242-Chlorotrityl chlorideHCID 2724699PyBOP

생성물 1

HCID 688146835-(Methyl-propylcarbamoyl)-nicotinic acid수율 50%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

Add a solution of pyridine-3,5-dicarboxylic acid (220 mg, 1.32 mmol), diisopropylethylamine (918 μL, 5.28 mmol), and DMF (1.5 mL) in dichloromethane (10 mL) to 2-chlorotritylchloride resin (11.0 g, 1.1 mmol) in a peptide synthesis vessel and mix for 3 h. Filter and wash the resin with a 17:2:1 mixture of dichloromethane:methanol:diisopropylethylamine, followed by dichloromethane. Add a solution of methylpropylamine (225 μL, 2.2 mmol), and benzotriazole-1-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (1.14 g, 2.2 mmol) in dichloromethane (10 mL) to the resin and mix for 1 h. Filter and wash the resin with dichloromethane (2×10 mL). Add a solution of 5% trifluoroacetic acid in dichloromethane (10 mL) to the resin and let stand for 10 min. Filter the resin and wash with dichloromethane (2×10 mL). Combine the filtrates and concentrate to give the title compound (110 mg, 50%).

후처리

  1. additionmix for 3 h
  2. filtrationFilter
  3. washwash the resin
  4. additionwith a 17:2:1 mixture of dichloromethane
  5. additionmix for 1 h
  6. filtrationFilter
  7. washwash the resin with dichloromethane (2×10 mL)
  8. additionAdd a solution of 5% trifluoroacetic acid in dichloromethane (10 mL) to the resin
  9. filtrationFilter the resin
  10. washwash with dichloromethane (2×10 mL)
  11. concentrationCombine the filtrates and concentrate

출처 및 근거

ORD 기록
ord-aa4c1324c6854311a3789bd9956d10df
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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