Methylamine → N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamide

HRID 1425856ノート

反応式

HRID 1425856 の反応式
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=12.CN([C:16]([O:20][N:21]1N=NC2C=CC=N[C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN>C(Cl)Cl.O>[CH3:16][O:20][N:21]([CH3:22])[C:10]([C:8]1[CH:7]=[CH:6][C:5]2=[N:1][O:2][N:3]=[C:4]2[CH:9]=1)=[O:12]

参加物

6

反応物 3

HCID 6329MethylamineHCID 27354542,1,3-Benzoxadiazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 59354764N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamide収率 79.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of benzo[c][1,2,5]oxadiazole-5-carboxylic acid (0.49 g, 2.987 mmol) in DCM (50 mL) were added HATU (1.7 g, 4.481 mmol), N-methoxy, N-methylamine (0.44 g, 4.481 mmol) and TEA (914 mg, 8.963 mmol) at RT under a nitrogen atmosphere. The reaction mixture was then stirred at RT for 3 h, diluted with water and the aqueous layer was extracted with DCM (3×50 mL). The combined organic extracts were washed with water (50 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamide (0.49 g, 79%) as a yellow oil.

後処理

  1. extractionthe aqueous layer was extracted with DCM (3×50 mL)
  2. washThe combined organic extracts were washed with water (50 mL) and brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-7610bd9a81b643a09ea7515baf2b0fd1
出典データセット
uspto-grants-2015_01
特許番号
US08933074B2

反応ノート

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