Ethyl Acetate → 3-Amino-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine

HRID 459896노트

반응식

HRID 459896 반응식
[N:1]([CH:4]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:7]=2[N:6]([CH2:22][C:23]([F:26])([F:25])[F:24])[C:5]1=[O:27])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1.O.[Cl-].[Na+].O>[NH2:1][CH:4]1[N:10]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:7]=2[N:6]([CH2:22][C:23]([F:26])([F:24])[F:25])[C:5]1=[O:27]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 184442503-Azido-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine

생성물 1

HCID 184442493-Amino-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine수율 51.9%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 3-azido-9-chloro-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (0.320 g, 0.812 mmol) and triphenylphosphine (0.426 g, 1.62 mmol) in tetrahydrofuran (13 mL) and water (1.5 mL) was stirred at room temperature for 48 h. Workup with ethyl acetate and saturated sodium bicarbonate, followed by saturated brine and drying over sodium sulfate gave the product. The crude product was purified by chromatography (silica gel, 0–5% methanol in methylene chloride gradient elution), giving the title compound (0.155 g). 1H NMR (500 MHz, CDCl3) δ 7.65 (d, J=8 Hz, 2H), 7.49 (tt, J=2,7 Hz, 1H), 7.42 (t, J=8 Hz, 2H), 7.32 (t, J=8 Hz, 1H), 7.26 (d, J=7 Hz, 1H), 5, 22 (m, 1H), 4.56 (s, 1H), 4.30 (m, 1H), 2.15 (br s, 2H).

후처리

  1. dry with materialdrying over sodium sulfate
  2. customgave the product
  3. customThe crude product was purified by chromatography (silica gel, 0–5% methanol in methylene chloride gradient elution)

출처 및 근거

ORD 기록
ord-f41423c6ae02483f81a2d839fcdb4be1
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196079B2

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