Trichloroacetonitrile → 3-chloro-4-[(3,4-dimethoxyphenyl)methoxy]-N-methyl-N-[2-[[(1-methylethyl)amino]carbonyl]-4-phenoxyphenyl]-benzamide

HRID 2099979

반응식

HRID 2099979 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[Cl:17].ClC(Cl)(Cl)C#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:48]([NH:51][C:52](=[O:68])[C:53]1[CH:58]=[C:57]([O:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH:56]=[CH:55][C:54]=1[NH:66][CH3:67])([CH3:50])[CH3:49]>C(Cl)Cl.C1COCC1>[Cl:17][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[O:7][CH2:6][C:5]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]([N:66]([CH3:67])[C:54]1[CH:55]=[CH:56][C:57]([O:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:58][C:53]=1[C:52]([NH:51][CH:48]([CH3:49])[CH3:50])=[O:68])=[O:14]

참가 물질

7

반응물 4

HCID 11011Trichloroacetonitrile2회HCID 11776Triphenylphosphine2회HCID 57796896N-isopropyl-2-(methylamino)-5-phenoxybenzamideHCID 577968974-(3,4-Dimethoxybenzyloxy)-3-chlorobenzoic acid

생성물 1

HCID 577968883-chloro-4-[(3,4-dimethoxyphenyl)methoxy]-N-methyl-N-[2-[[(1-methylethyl)amino]carbonyl]-4-phenoxyphenyl]-benzamide수율 87.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A slurry of 1B (28 mg, 0.09 mmol) and trichloroacetonitrile (0.009 mL, 0.09 mmol) in CH2Cl2 (1 mL) at room temperature was treated with a solution of triphenylphosphine (22 mg, 0.09 mmol) in THF (0.25 mL). The reaction mixture was stirred for 30 minutes and additional trichloroacetonitrile (0.009 mL, 0.09 mmol) and triphenylphosphine (22 mg, 0.09 mmol) were added. The resulting solution was treated with 44B (16 mg, 0.06 mmol) in CH2Cl2 (0.5 mL). The stirring was continued for 2 hours, and then the reaction concentrated to dryness. The residue was purified by chromatography (SiO2, 50% to 75% EtOAc in hexanes) to afford 44C (31 mg).

후처리

  1. waitThe stirring was continued for 2 hours
  2. concentrationthe reaction concentrated to dryness
  3. customThe residue was purified by chromatography (SiO2, 50% to 75% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-2c90fc973cc74432bb313e260acb7af5
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569725B2

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