Triethylamine → Methyl 6-[(3-{[(benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylate

HRID 446504노트

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HRID 446504 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].[CH2:14]([N:16](CC)CC)C.C(Cl)(=O)C(C)(C)C.CN[CH:30]([NH:33][CH3:34])[CH2:31][CH3:32].[CH2:35]([O:42][C:43](Cl)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH2:35]([O:42][C:43]([N:16]([CH3:14])[CH2:32][CH2:31][CH2:30][N:33]([CH3:34])[C:11]([C:8]1[N:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)=[O:13])=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

7

반응물 5

HCID 8471Triethylamine2회HCID 10387Benzyl chloroformateHCID 62493Pivaloyl chlorideHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 22287041HCID 22287041, 화합물

생성물 1

HCID 66671574Methyl 6-[(3-{[(benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylate수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

5-(Methoxycarbonyl)pyridine-2-carboxylic acid (700 mg, 3.86 mmol) was dissolved in methylene chloride (40 mL), triethylamine (0.805 mL, 5.79 mmol) and pivaloyl chloride (0.524 mL, 4.25 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added dropwise to a solution of N,N′-dimethylpropanediamine (1.18 g, 11.6 mmol) in methylene chloride (40 mL) under ice cooling, and the mixture was stirred overnight at room temperature. Triethylamine (4.03 mL, 29.0 mmol) and benzyloxycarbonyl chloride (4.14 mL, 29.0 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:3→0:100, v/v) to give the title compound (1.23 g; yield, 80%) as a colorless oily substance.

후처리

  1. stirringthe mixture was stirred overnight at room temperature
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (hexane

출처 및 근거

ORD 기록
ord-b5c48cd6865443eebb047be2d85aa929
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

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