Diisopropylethylamine → Methyl 2-methyl-2-(5-methyl-6-(2,2,2-trifluoroethoxy)picolinamido)propanoate

HRID 927335

반응식

HRID 927335 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]([OH:16])=O)=[N:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].Cl.[CH3:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[NH2:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:23][C:21]([NH:22][C:14](=[O:16])[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:7]([O:8][CH2:9][C:10]([F:11])([F:12])[F:13])[N:6]=1)([CH3:24])[C:20]([O:19][CH3:18])=[O:25]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 710875095-Methyl-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

생성물 1

HCID 71087523Methyl 2-methyl-2-(5-methyl-6-(2,2,2-trifluoroethoxy)picolinamido)propanoate수율 123.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-methyl-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (30 mg, 128 μmol), 2-methyl-alanine methyl ester hydrochloride (23.5 mg, 153 μmol), HATU (CAN 148893-10-1, 97.0 mg, 255 μmol) and DIEA (82.4 mg, 109 μl, 638 μmol) in DMF was stirred at ambient temperature for 72 h. The crude reaction mixture was concentrated in vacuo to give 53 mg of a yellow solid. This solid was purified by preparative TLC (silica gel, 2.0 mm, 1:1 heptane/i-PrOAc) and eluted from the silica gel with i-PrOAc. Filtration over speedex and evaporation under reduced pressure provided the title compound (10 mg, 23%) as colorless liquid, MS (EI): m/e=335.2 [M+H]+.

후처리

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo

출처 및 근거

ORD 기록
ord-05e699a02409423684e27be35afb8149
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290451B2

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