1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → Regorafenib

HRID 475440노트

반응식

HRID 475440 반응식
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([F:19])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31]>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:28]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:30]([F:32])([F:31])[F:33])[CH:23]=3)=[O:29])=[C:14]([F:19])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

참가 물질

4

반응물 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 468352194-(4-Amino-3-fluorophenoxy)-N-methylpyridine-2-carboxamide

생성물 1

HCID 11167602Regorafenib수율 47.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methylamide (177 mg, 0.68 mmol) in toluene (3 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (150 mg, 0.68 mmol). The mixture was stirred at rt for 72 h. The reaction was concentrated under reduced pressure and the residue was triturated with diethylether. The resulting solid was collected by filtration and dried in vacuo for 4 h to afford the title compound (155 mg, 0.32 mmol; 47% yield); 1H-NMR (DMSO-d6) 2.78 (d, J=4.9, 3H), 7.03-7.08 (m, 1H), 7.16 (dd, J=2.6, 5.6, 1H), 7.32 (dd, J=2.7, 11.6, 1H), 7.39 (d, J=2.5, 1H), 7.60 (s, 2H), 8.07-8.18 (m, 2H), 8.50 (d, J=5.7, 1H), 8.72 (s, 1H), 8.74-8.80 (m, 1H), 9.50 (s, 1H); MS (HPLC/ES) 483.06 m/z=(M+1).

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was triturated with diethylether
  3. filtrationThe resulting solid was collected by filtration
  4. customdried in vacuo for 4 h

출처 및 근거

ORD 기록
ord-a0df1dc4c8a148b386b384380c4fcb5a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637553B2

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