Cyanogen Bromide → [6-(5-Amino-[1,3,4]oxadiazol-2-yl)-4-fluoro-1H-benzoimidazol-5-yl]-(4-bromo-2-methyl-phenyl)-amine

HRID 1010028

반응식

HRID 1010028 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:19]([NH:21][NH2:22])=[O:20])=[CH:11][C:12]3[NH:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([CH3:23])[CH:3]=1.[N:24]#[C:25]Br.C([O-])(O)=O.[Na+]>O1CCOCC1.C(Cl)Cl.O.[Cl-].[Na+].O>[NH2:24][C:25]1[O:20][C:19]([C:10]2[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[CH3:23])=[C:17]([F:18])[C:13]3[N:14]=[CH:15][NH:16][C:12]=3[CH:11]=2)=[N:21][N:22]=1

참가 물질

8

반응물 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 668979206-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid hydrazide

생성물 1

HCID 10150820[6-(5-Amino-[1,3,4]oxadiazol-2-yl)-4-fluoro-1H-benzoimidazol-5-yl]-(4-bromo-2-methyl-phenyl)-amine수율 55%

시약·촉매·용매 4

HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

실험 절차

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid hydrazide 20a (0.041 g, 0.109 mmol) is suspended in 1,4-dioxane (1.5 mL) and 36 μL of a 3 M solution of cyanogen bromide in methylene chloride is added. NaHCO3 (9 mg, 0.109 mmol) in water (1.5 mL) is then added. After 16 hours, the reaction mixture is diluted with water and brine and extracted with THF. The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure. Purification by FCC eluted with 98:2 ethyl acetate:MeOH provides 24 mg (55%) of pure desired product as a yellow solid: LC/MS ESI (+) m/z 403, 405 (M+ Br pattern) detected;

후처리

  1. extractionextracted with THF
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification by FCC
  5. washeluted with 98:2 ethyl acetate

출처 및 근거

ORD 기록
ord-73e4f647e5e24e4ab91138b0988d45ce
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973170B2

연결된 노트

불러오는 중…