Acetyl chloride → 1-[5-Aminomethyl-1-(4-hydroxy-butyl)-1H-benzoimidazol-2-ylmethyl]-4-methoxy-1H-quinolin-2-one

HRID 896365노트

반응식

HRID 896365 반응식
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:30][CH2:31][CH2:32][CH2:33][OH:34])[C:14]([CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([O:27][CH3:28])=[CH:19][C:18]3=[O:29])=[N:15][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)(=O)C>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:30][CH2:31][CH2:32][CH2:33][OH:34])[C:14]([CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([O:27][CH3:28])=[CH:19][C:18]3=[O:29])=[N:15][C:11]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 69717811[1-(4-hydroxy-butyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 444336091-[5-Aminomethyl-1-(4-hydroxy-butyl)-1H-benzoimidazol-2-ylmethyl]-4-methoxy-1H-quinolin-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled (0° C.) suspension of [1-(4-hydroxy-butyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (74 mg, 0.15 mmol) in DCM (3 mL) was added TFA (337 μL, 4.38 mmol). The solution was allowed to stir for 6 h at room temperature, followed by the removal of the volatiles in vacuo. The resulting trifluoroacetate was dissolved in methanol (3 mL) followed by the addition of acetyl cloride (104 μL, 1.46 mmol). After 10 minutes the solution was concentrated. This procedure was repeated allowing the reaction to run for 3 hrs. The solution was concentrated in vacuo and the residue stripped with methanol (twice) to yield 1-[5-Aminomethyl-1-(4-hydroxy-butyl)-1H-benzoimidazol-2-ylmethyl]-4-methoxy-1H-quinolin-2-one; HCl salt (65 mg, 100%) as an off white solid:

후처리

  1. temperatureTo a cooled
  2. customfollowed by the removal of the volatiles in vacuo
  3. dissolutionThe resulting trifluoroacetate was dissolved in methanol (3 mL)
  4. concentrationAfter 10 minutes the solution was concentrated
  5. customthe reaction
  6. waitto run for 3 hrs
  7. concentrationThe solution was concentrated in vacuo

출처 및 근거

ORD 기록
ord-b774b5335ab445268cc923d824988137
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919331B2

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