1H-1,2,4-Triazole → HCID 59313851, 화합물

HRID 889423

반응식

HRID 889423 반응식
Br[C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[O:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].[NH:23]1[CH:27]=[N:26][CH:25]=[N:24]1>CN1C(=O)CCC1.ClCCl.[Cu]I>[CH3:9][N:8]([CH3:10])[CH2:7][CH2:6][O:5][C:4]1[CH:3]=[C:2]([N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=1

참가 물질

7

반응물 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 593139932-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamine

생성물 1

HCID 59313851HCID 59313851, 화합물수율 57%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Intermediate 16A (200 mg, 0.69 mmol), copper(I) iodide (65.9 mg, 0.35 mmol), potassium carbonate (287 mg, 2.1 mmol) and 1H-1,2,4-triazole (143 mg, 2.075 mmol) in NMP (2 mL) were heated at 120° C. for 6 hours. The reaction mixture was diluted with dichloromethane, and filtered through a plug of silica gel and washed with ethyl acetate. The filtrate was concentrated, and the residue was purified by reverse phase HPLC to obtain Intermediate 16B (109 mg, 56.8% yield) as a yellow solid. HPLC: Rt=0.74 min. (PHENOMENEX® Luna 5 micron C18 4.6×30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate=5 mL/min, detection at 254 nm). MS (ES): m/z=278.08 [M+H]+.

후처리

  1. filtrationfiltered through a plug of silica gel
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-9cd1b105d2e44f558f20b82ae5ba426f
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252795B2

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