Triethylamine → N-(1H-benzimidazol-2-yl)-2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide

HRID 1280038

반응식

HRID 1280038 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([OH:15])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:56][C:57]1[NH:58][C:59]2[CH:65]=[CH:64][CH:63]=[CH:62][C:60]=2[N:61]=1>C(Cl)Cl>[NH:58]1[C:59]2[CH:65]=[CH:64][CH:63]=[CH:62][C:60]=2[N:61]=[C:57]1[NH:56][C:13](=[O:15])[CH:12]([C:4]1[CH:5]=[CH:6][C:7]([S:8]([CH3:11])(=[O:9])=[O:10])=[C:2]([Br:1])[CH:3]=1)[CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 136242-AminobenzimidazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 120676662-(3-Bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

생성물 1

HCID 10278076N-(1H-benzimidazol-2-yl)-2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide수율 53%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (100 mg, 0.266 mmol), triethylamine (110 μL, 0.80 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (187 mg, 0.42 mmol), and 2-aminobenzimidazole (56 mg, 0.42 mmol) in methylene chloride (10 mL) was stirred at 25° C. for 1.5 h. The reaction mixture was partitioned between water and methylene chloride. The organic layer was washed sequentially with a 1N aqueous hydrochloric acid solution (1×mL), water (1×10 mL), and a saturated aqueous sodium bicarbonate solution (1×10 mL). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 19/1 chloroform/methanol) afforded N-(1H-benzoimidazol-2-yl)-2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (69 mg, 53%) as a white solid: mp>220° C.; EI-HRMS m/e calcd for C22H24BrN3O3S (M+) 489.0722, found 489.0727.

후처리

  1. customThe reaction mixture was partitioned between water and methylene chloride
  2. washThe organic layer was washed sequentially with a 1N aqueous hydrochloric acid solution (1×mL), water (1×10 mL)
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6a169bc1fff1420a9e60ee274c1e39a0
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448399B1

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