1,2-Dichloroethane → 3-chloro-4-methoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide

HRID 418340

反応式

HRID 418340 の反応式
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([OH:9])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:29][CH2:30][C:31]1[CH:32]=[C:33]([CH:48]=[CH:49][CH:50]=1)[C:34]([NH:36][C:37]1[CH:46]=[C:45]2[C:40]([CH2:41][CH2:42][N:43]([CH3:47])[CH2:44]2)=[CH:39][CH:38]=1)=[O:35]>CN(C=O)C.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([NH:29][CH2:30][C:31]1[CH:50]=[CH:49][CH:48]=[C:33]([C:34](=[O:35])[NH:36][C:37]2[CH:46]=[C:45]3[C:40]([CH2:41][CH2:42][N:43]([CH3:47])[CH2:44]3)=[CH:39][CH:38]=2)[CH:32]=1)=[O:9]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 591908413-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamideHCID 666490683-Chloro-4-methoxybenzoic acid dihydrochloride

生成物 1

HCID 591908573-chloro-4-methoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 3-chloro-4-methoxybenzoic acid dihydrochloride (29 mg, 150 mmol), EDC (30 mg, 150 mmol), HOBt (22 mg, 150 mmol), and TEA (0.057 mL, 408 mmol) in anhydrous DMF (5 mL) was stirred at room temperature for 30 min. To this was added 3-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide. (50 mg, 136 mmol) and the solution stirred at room temperature for 24 h. The reaction was diluted EtOAc (100 mL) and quenched with sat. NH4Cl (100 mL). The organic fraction was dried (Na2SO4). The residue was purified by flash chromatography using a methanol/methylene chloride gradient to provide 31 mg of 3-chloro-4-methoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide. MS, electrospray, 464 (M+H).

後処理

  1. customquenched with sat. NH4Cl (100 mL)
  2. dry with materialThe organic fraction was dried (Na2SO4)
  3. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-0de0ffccb47347d3bd615425be5c317b
出典データセット
uspto-grants-2012_01
特許番号
US08093266B2

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