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

HRID 418340노트

반응식

HRID 418340 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-0de0ffccb47347d3bd615425be5c317b
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093266B2

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