Diisopropylethylamine → Methyl 3,3-dimethyl-2-(4-(picolinamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801298노트

반응식

HRID 1801298 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](Cl)=[O:40]>ClCCl>[CH3:19][C:17]1([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=2)[NH:9][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:39](=[O:40])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=2)=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 67441380Methyl 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

생성물 1

HCID 67442750Methyl 3,3-dimethyl-2-(4-(picolinamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate수율 52.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (100 mg, 0.32 mmol) and N,N-diisopropylethylamine (0.11 mL, 0.64 mmol) in dichloromethane (5 mL) was added freshly prepared picolinoyl chloride (56 mg, 0.35 mmol) with ice cooling. Upon completion of addition, the resultant deep blue solution was allowed to warm back to room temperature and stir overnight. LC-MS showed the reaction was complete. Solvent was removed in vacuo and the residue was purified by preparative Thin layer chromatography to afford 70 mg of methyl 3,3-dimethyl-2-(4-(picolinamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as a white solid. Yield: 52%. MS (ESI+APCI) M+1=416.20.

후처리

  1. additionUpon completion of addition
  2. customSolvent was removed in vacuo
  3. customthe residue was purified by preparative Thin layer chromatography

출처 및 근거

ORD 기록
ord-a54a06586adb43dc94eb66ccafc8e051
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344137B2

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