4-Chloro-1,2-diaminobenzene → N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide

HRID 1500948노트

반응식

HRID 1500948 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[F:10][C:11]([F:20])([F:19])[C:12]([OH:18])([CH3:17])[CH2:13][C:14](O)=[O:15].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>O.CN(C=O)C>[NH2:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:14](=[O:15])[CH2:13][C:12]([OH:18])([CH3:17])[C:11]([F:20])([F:19])[F:10]

참가 물질

7

반응물 4

HCID 72634-Chloro-1,2-diaminobenzeneHCID 81531DiisopropylethylamineHCID 1361684,4,4-Trifluoro-3-hydroxy-3-methylbutanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 89924350N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide수율 76.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-chlorobenzene-1,2-diamine (1.32 g, 9.3 mmol), 4,4,4-trifluoro-3-hydroxy-3-methylbutanoic acid (1.6 g, 9.3 mmol), HATU (4.24 g, 11.2 mmol), DIPEA (3.1 mL, 18.6 mmol) and DMF (25 mL) was stirred at room temperature overnight. The mixture was diluted with water (150 mL), and then extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL), and then dried over Na2SO4, then filtered and concentrated. The residue was purified with flash column (30% EtOAc in PE to EtOAc) to give N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide as brown oil (2.1 g, 76%).

후처리

  1. extractionextracted with EtOAc (50 mL×3)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with flash column (30% EtOAc in PE to EtOAc)

출처 및 근거

ORD 기록
ord-48d24de882be453ba1e9a38caa36dca2
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206191B2

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