Potassium Carbonate → N-(4-Methoxybenzyl)-N-((naphthalen-2-yl)methyl)-3H-benzo[d]imidazol-5-amine

HRID 45970

반응식

HRID 45970 반응식
C([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:16][C:11]=2[N:10]=[CH:9]1)(OC(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+].[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[CH2:43]Br>CN(C=O)C.O>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:17]([CH2:43][C:34]2[CH:35]=[CH:36][C:37]3[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:33]=2)[C:15]2[CH:14]=[CH:13][C:12]3[N:8]=[CH:9][NH:10][C:11]=3[CH:16]=2)=[CH:24][CH:23]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 67443969N1-Boc-N-(4-methoxybenzyl)benzimidazol-5-amine

생성물 1

HCID 53496317N-(4-Methoxybenzyl)-N-((naphthalen-2-yl)methyl)-3H-benzo[d]imidazol-5-amine

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

N1-Boc-N-(4-methoxybenzyl)benzimidazol-5-amine (353 mg; 1 mmol; 1 eq.) was dissolved in DMF (5 ml), treated with K2CO3 (166 mg; 1.2 mmol; 1.2 eq.) and naphthalen-2-yl-methyl-bromide (265 mg; 1.2 mmol; 1.2 eq.) and stirred at room temperature for 24 h. The mixture was diluted with water and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The remains were taken up with THF (5 ml), treated with 5 N NaOCH3 and stirred for 2 h at room temperature. The mixture was diluted with water and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient. Yield: 0.058 mg (14.8%); MS m/z: 394.2 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 3.70 (s, 3H); 4.68 (s, 2H); 4.80 (s, 2H); 6.76 (d, 1H, 4J=2.1 Hz); 6.82 (dd, 1H, 4J=2.3 Hz, 3J=8.9 Hz); 6.87-6.89 (m, 2H); 7.22-7.24 (m, 2H); 7.34 (d, 1H, 3J=8.9 Hz); 7.43-7.47 (m, 5H); 7.75 (br s, 1H); 7.79-7.81 (m, 1H); 7.85-7.87 (m 2H); 7.94 (s, 1H); HPLC (METHOD [A]): rt 18.12 min (95.6%)

후처리

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated
  4. additiontreated with 5 N NaOCH3
  5. stirringstirred for 2 h at room temperature
  6. additionThe mixture was diluted with water
  7. extractionextracted with ethyl acetate (3×25 ml)
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica using a CHCl3/MeOH gradient
  11. customrt 18.12 min (95.6%)

출처 및 근거

ORD 기록
ord-3c2503047a9645b58aec9199ffd5302f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541596B2

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