Methanol → 2-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-isonicotinamide

HRID 1945455

반응식

HRID 1945455 반응식
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19]([NH2:21])=[O:20].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CO>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19]([NH2:21])=[O:20])=[O:8]

참가 물질

7

반응물 4

HCID 887MethanolHCID 1480Trichlorophenoxyacetic acidHCID 3516532-AminoisonicotinamideHCID 2724699PyBOP

생성물 1

HCID 580013202-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-isonicotinamide수율 41.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To solution of (2,4,5-trichloro-phenoxyacetic acid (100 mg, 0.39 mmol), 2-amino isonicotinamide (107 mg, 0.78 mmol) and DMAP (96.22 mg, 0.78 mmol) in DMF 12 ml was added PyBOP (409.7 mg, 0.78 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by PLC (EtoAC:Hexane:MeOH=3:6:1-2:4:1) to afford 2-[2-(2,4,5-trichloro-phenoxy)-acetylamino]-isonicotinamide as a colorless solid (0.06 g, 41% yield).

후처리

  1. customReaction mixture
  2. additionwas poured onto ice cold water
  3. customThe organic phase was separated
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by PLC (EtoAC:Hexane:MeOH=3:6:1-2:4:1)

출처 및 근거

ORD 기록
ord-474952af8a0f467a9705947702d17dea
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

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