Dimethylformamide → 4-Amino-3-fluoro-N-[2-(4-fluorophenoxy)-2-methylpropyl]benzamide

HRID 401826

반응식

HRID 401826 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.C(N(CC)C(C)C)(C)C.[F:50][C:51]1[CH:62]=[CH:61][C:54]([O:55][C:56]([CH3:60])([CH3:59])[CH2:57][NH2:58])=[CH:53][CH:52]=1>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:58][CH2:57][C:56]([O:55][C:54]2[CH:53]=[CH:52][C:51]([F:50])=[CH:62][CH:61]=2)([CH3:60])[CH3:59])=[O:8])=[CH:4][C:3]=1[F:11]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 99714-Amino-3-fluorobenzoic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28917627HCID 28917627, 화합물

생성물 1

HCID 577322414-Amino-3-fluoro-N-[2-(4-fluorophenoxy)-2-methylpropyl]benzamide

실험 절차

To a mixture of 4-amino-3-fluorobenzoic acid (200.0 mg, 1.289 mmol) and HBTU (490 mg, 1.3 mmol) in DMF (2 mL, 20 mmol) at 0° C. were added N,N-diisopropylethylamine (0.67 mL, 3.9 mmol) and 2-(4-fluorophenoxy)-2-methylpropan-1-amine (Preparation 91, 280 mg, 1.5 mmol). The reaction mixture was slowly warmed to ambient temperature. The reaction mixture was quenched with an equal volume of saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic layers were washed successively with water, aqueous lithium chloride, and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on the Isco (120 g cartridge, chloroform to 12% MeOH in chloroform).

후처리

  1. customThe reaction mixture was quenched with an equal volume of saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed successively with water, aqueous lithium chloride, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on the Isco (120 g cartridge, chloroform to 12% MeOH in chloroform)

출처 및 근거

ORD 기록
ord-22e8725fd6f5442f8a53030995a82137
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741934B2

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