2-Pyrazinecarboxylic acid → Methyl 2-(bis-(tert-butoxycarbonyl)amino)-3-(pyrazine-2-carboxamido)benzoate

HRID 520445노트

반응식

HRID 520445 반응식
[NH2:1][C:2]1[C:3]([N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[C:33](O)=[O:34].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.O>[C:23]([O:22][C:20]([N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[C:3]1[C:2]([NH:1][C:33]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][N:27]=2)=[O:34])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[O:21])([CH3:26])([CH3:25])[CH3:24]

참가 물질

7

반응물 4

HCID 10472-Pyrazinecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58552839Methyl 3-amino-2-(bis(tert-butoxycarbonyl)amino)benzoate

생성물 1

HCID 58552825Methyl 2-(bis-(tert-butoxycarbonyl)amino)-3-(pyrazine-2-carboxamido)benzoate수율 58.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of methyl 3-amino-2-(bis(tert-butoxycarbonyl)amino)benzoate 13 (3.8 g, 10.4 mmol), pyrazine-2-carboxylic acid 10 (1.54 g, 12.5 mmol), HATU (7.9 g, 20.8 mmol) and DIPEA (2.68 g, 20.8 mmol) in DMF was heated at 50° C. for 12 h. The reaction mixture was poured into H2O and the resulting precipitate was collected by filtration and dried under vacuum. The crude residue was purified by flash chromatography to give 14 (2.87 g, 58% yield)

후처리

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under vacuum
  3. customThe crude residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-75f2ef6ebe1d4488bc688f9e05dbe96f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326986B2

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