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 574208노트

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HRID 574208 반응식
[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

참가 물질

6

반응물 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)picolinohydrazide2회

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
0 °C

실험 절차

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;

후처리

  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)

출처 및 근거

ORD 기록
ord-56477a2ddc4c48b4b2d9dafe154eb50d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034879B2

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