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

HRID 896365ノート

反応式

HRID 896365 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-b774b5335ab445268cc923d824988137
出典データセット
uspto-grants-2005_07
特許番号
US06919331B2

反応ノート

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