4-Chloro-N-methoxy-N-methylbenzamide → HCID 57754508, 화합물

HRID 227132

반응식

HRID 227132 반응식
I[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)[CH:3]=1.C([Mg]Cl)(C)C.[Cl:26][C:27]1[CH:38]=[CH:37][C:30]([C:31](N(OC)C)=[O:32])=[CH:29][CH:28]=1>C1COCC1>[Cl:26][C:27]1[CH:38]=[CH:37][C:30]([C:31]([C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=3)[CH:3]=2)=[O:32])=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 112756634-Chloro-N-methoxy-N-methylbenzamideHCID 57754594HCID 57754594, 화합물HCID 178418918HCID 178418918, 화합물

생성물 1

HCID 57754508HCID 57754508, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A −78° C. solution of 3-iodo-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one (113 mg, 0.3 mmol, 1 equiv) in 3 mL of THF was treated with 1.65 mL of isopropyl magnesium chloride (1.1 equiv) for 2 hours. Then 4-chloro-N-methoxy-N-methyl-benzamide (46 μL, 1.2 equiv) was added and stirring continued at rt for 2 hours. The reaction was quenched by slow addition of saturated aqueous solution of NH4Cl. Standard workup followed by HPLC purification gave 3-(4-chloro-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one. LCMS (ES) M+H 389.1

후처리

  1. customThe reaction was quenched by slow addition of saturated aqueous solution of NH4Cl
  2. customStandard workup followed by HPLC purification

출처 및 근거

ORD 기록
ord-d961c6c925004b469a725430bff2407b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557213B2

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