Isoamylamine → 2-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-benzamide

HRID 925260노트

반응식

HRID 925260 반응식
[F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:3][CH2:4][S:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:54][CH:55]([CH3:59])[CH2:56][CH2:57][NH2:58]>O1CCCC1>[F:22][C:2]([F:1])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:3][CH2:4][S:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH:58][CH2:57][CH2:56][CH:55]([CH3:59])[CH3:54])=[O:10]

참가 물질

6

반응물 4

HCID 7894IsoamylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867201602-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-benzoic acid

생성물 1

HCID 762874042-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-benzamide수율 56.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-benzoic acid (0.24 g, 0.73 mmol) in dry tetrahydrofuran (10 ml) are added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.30 g, 0.80 mmol) and triethylamine (0.38 ml, 2.2 mmol) at RT. The reaction mixture is stirred for 5 min at RT followed by the addition of 3-methyl-butyl-amine (0.1 ml, 0.88 mmol). The reaction mixture is stirred at RT for 2 h. After completion of the reaction, the solvent is distilled off and the residue is diluted with saturated sodium hydrogen carbonate solution (20 ml) before extraction with EtOAc (3×30 ml). The organic layer is washed with saturated ammonium chloride solution (30 ml), water (30 ml), brine (30 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude product, which is purified by column chromatography (silica gel, 50% EtOAc/hexane) to yield 2-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-N-(3-methyl-butyl)-benzamide (example 1) (0.16 g, 0.41 mmol, 56%). [M+H]+ 396.1.

후처리

  1. stirringThe reaction mixture is stirred at RT for 2 h
  2. customAfter completion of the reaction
  3. distillationthe solvent is distilled off
  4. additionthe residue is diluted with saturated sodium hydrogen carbonate solution (20 ml) before extraction with EtOAc (3×30 ml)
  5. washThe organic layer is washed with saturated ammonium chloride solution (30 ml), water (30 ml), brine (30 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customto get the crude product, which
  9. customis purified by column chromatography (silica gel, 50% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-62a75deee79a437cbc9ee4849c6a3a15
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284286B2

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