3,5-Dimethylaniline → 2-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

HRID 1984713

反応式

HRID 1984713 の反応式
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[C:37]([CH2:39][S:40][C:41]2[C:46]([C:47]([OH:49])=O)=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:36]=[CH:35][N:34]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[NH2:50][C:51]1[CH:56]=[C:55]([CH3:57])[CH:54]=[C:53]([CH3:58])[CH:52]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:25]([O:29][C:30]([NH:32][C:33]1[CH:38]=[C:37]([CH2:39][S:40][C:41]2[C:46]([C:47]([NH:50][C:51]3[CH:56]=[C:55]([CH3:57])[CH:54]=[C:53]([CH3:58])[CH:52]=3)=[O:49])=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:36]=[CH:35][N:34]=1)=[O:31])([CH3:27])([CH3:28])[CH3:26]

参加物

7

反応物 4

HCID 79493,5-DimethylanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 231509762-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid

生成物 1

HCID 112482792-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (630 mg, 1.7 mmol) was added to a solution of 2-(2-tert-butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid (Reference compound No. 9-1, 500 mg, 1.4 mmol), 3,5-xylidine (180 mg, 1.5 mmol) and N,N-diisopropylethylamine (0.72 mL, 4.1 mmol) in N,N-dimethylformamide (7 mL) at room temperature, and the mixture was stirred for 12 hours. Ethyl acetate (30 mL) was added to the reaction mixture, then the whole was washed with brine (50 mL) and dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, then the resulting residue was purified by silica gel column chromatography to give 670 mg of the target compound quantitatively as a colorless solid.

後処理

  1. washthe whole was washed with brine (50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe organic layer was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f772678dc6d54076a5ed56384050d816
出典データセット
uspto-grants-2009_06
特許番号
US07544703B2

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