3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid → 3-Amino-6-bromo-N'-(3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl)-5-(trifluoromethyl)picolinohydrazide

HRID 574208ノート

反応式

HRID 574208 の反応式
[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH2:16])=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:17][C:18]([F:26])([F:25])[C:19]([OH:24])([CH3:23])[C:20](O)=[O:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1.CO>[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:20](=[O:21])[C:19]([OH:24])([CH3:23])[C:18]([F:26])([F:25])[F:17])=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

参加物

6

反応物 3

HCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867295953-Amino-6-bromo-5-(trifluoromethyl)picolinohydrazide2 回

生成物 1

HCID 867295963-Amino-6-bromo-N'-(3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl)-5-(trifluoromethyl)picolinohydrazide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

A cooled (0° C.) solution of 3-amino-6-bromo-5-(trifluoromethyl)picolinohydrazide (Intermediate H) (15 g, 50.2 mmol) in dry NMP (50 ml) was treated with 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (8.72 g, 55.2 mmol), HATU (20.98 g, 55.2 mmol) followed by dropwise addition of TEA (15.38 ml, 110 mmol) over 10 minutes. The orange solution was stirred at 0° C. and allowed to warm to RT and stirred for 3 days. The reaction mixture was partitioned between EtOAc (200 mL) and 1M NaOH (200 mL), shaken and separated. The organic portion washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo to give an orange oil. The oil was taken up in methanol (50 mL) and triturated with water (300 mL) to afford the title compound as a yellow solid;

後処理

  1. temperatureto warm to RT
  2. stirringstirred for 3 days
  3. customThe reaction mixture was partitioned between EtOAc (200 mL) and 1M NaOH (200 mL)
  4. stirringshaken
  5. customseparated
  6. washThe organic portion washed with brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give an orange oil
  10. customtriturated with water (300 mL)

出典と根拠

ORDレコード
ord-56477a2ddc4c48b4b2d9dafe154eb50d
出典データセット
uspto-grants-2015_05
特許番号
US09034879B2

反応ノート

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