Dimethylformamide → N-[3-(2-methylimidazol-1-yl)propyl]-2-phenylbenzoxazole-4-carboxamide

HRID 506217노트

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HRID 506217 반응식
[C:1]1([C:7]2[O:8][C:9]3[C:10](=[C:12]([C:16]([OH:18])=O)[CH:13]=[CH:14][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.C(=O)(O)[O-].[Na+].[CH3:35][C:36]1[N:37]([CH2:41][CH2:42][CH2:43][NH2:44])[CH:38]=[CH:39][N:40]=1>C(Cl)Cl>[CH3:35][C:36]1[N:37]([CH2:41][CH2:42][CH2:43][NH:44][C:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=23)=[O:18])[CH:38]=[CH:39][N:40]=1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 31521053-(2-methyl-1H-imidazol-1-yl)propan-1-amineHCID 108683692-Phenylbenzoxazole-4-carboxylic acid

생성물 1

HCID 11674911N-[3-(2-methylimidazol-1-yl)propyl]-2-phenylbenzoxazole-4-carboxamide수율 14%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A 100-mL one-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 2-phenylbenzoxazole-4-carboxylic acid (0.190 g, 0.79 mmol), DMF (0.588 g, 8.00 mmol) and anhydrous methylene chloride (15 mL). The resulting solution was treated with oxalyl chloride (1.46 g, 11.5 mmol) dropwise over 5 min and stirred at ambient temperature under nitrogen for 2 h. After this time, the reaction mixture was evaporated to a solid residue which was dissolved in anhydrous methylene chloride (15 mL). The resulting solution was treated with sodium bicarbonate (0.672 g, 8.00 mmol) and stirred at ambient temperature under nitrogen for 15 min. After this time, a solution of 3-(2-methylimidazol-1-yl)propylamine (0.332 g, 2.39 mmol) in anhydrous methylene chloride (5 mL) was added and the mixture stirred for a further 20 h. The reaction mixture was then diluted with methylene chloride (50 mL) and washed with 10% aqueous potassium carbonate (10 mL) followed by water (20 mL). The organic phase was dried over sodium sulfate, filtered and evaporated to a solid residue which was further purified by preparative HPLC to give 0.040 g (14% yield) of N-[3-(2-methylimidazol-1-yl)propyl]-2-phenylbenzoxazole-4-carboxamide as a white solid: mp 145-148° C.; 1H NMR (300 MHz, CD3OD) δ 8.33 (m, 2H), 8.03 (dd, J=7.8, 0.9 Hz, 1H), 7.86 (dd, J=8.2, 0.9 Hz, 1H), 7.69-7.59 (m, 4H), 7.52 (t, J=8.0 Hz, 1H), 7.38 (d, J=2.1 Hz, 1H), 4.32 (t, J=7.1 Hz, 2H), 3.67 (t, J=7.1 Hz, 2H), 2.65 (s, 3H), 2.31 (m, 2H); MS (ESI) m/z 361 [M+H]+.

후처리

  1. customA 100-mL one-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customAfter this time, the reaction mixture was evaporated to a solid residue which
  4. dissolutionwas dissolved in anhydrous methylene chloride (15 mL)
  5. stirringstirred at ambient temperature under nitrogen for 15 min
  6. stirringthe mixture stirred for a further 20 h
  7. washwashed with 10% aqueous potassium carbonate (10 mL)
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to a solid residue which
  11. customwas further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-6440972e9de04ae8a68f5ad689b82d10
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781430B2

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