Sodium Iodide → 4-Methoxyquinoline-2-carboxamide

HRID 890402

반응식

HRID 890402 반응식
C(OC(N1CCN(C(C([NH:21][C:22]([C:24]2[CH:33]=[C:32]([O:34][CH3:35])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[O:23])CC2N=CNC=2)=O)CC1)=O)C.C(=O)([O-])[O-].[K+].[K+].[Na+].[I-]>CN(C=O)C>[NH2:21][C:22]([C:24]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1)=[O:23]

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 178473365HCID 178473365, 화합물

생성물 1

HCID 149256254-Methoxyquinoline-2-carboxamide수율 88.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-(imidazol-4-yl)ethyl]aminocarbonyl-4-methoxyquinoline (69 mg, 0.14 mmol) in DMF (2 mL) was added t-butyl bromo acetate (0.026 mL, 1.2 eq.), potassium carbonate (30 mg, 1.5 eq), NaI (2.0 mg, 0.1 eq.). The reaction mixture was heated at 50° C. for 1 hour. Evaporation followed by flash column chromatography with 2%–3% MeOH in methylene chloride afforded 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-(1-(t-butoxycarbonyl)methyl)imidazol-4-yl)ethyl]-aminocarbonyl-4-methoxyquinoline (25 mg) which was treated with neat trifluoroacetic acid (0.5 mL) for 1.5 hours at ambient temperature. Repeated evaporation of the solvents and treatment with methylene chloride afforded 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-(1-(carboxymethyl)imidazol-4-yl)ethyl]-aminocarbonyl-4-methoxyquinoline (27 mg) as a trifluoroacetic acide salt: NMR (DMSO) 1.20 (t, 3), 3.2–3.6 (m, 11), 4.05 (q, 2), 4.1 (s, 3), 5.0 (s, 2), 5.3 (m, 1), 7.45 (s, 1), 7.5 (s, 1), 7.65 (t, 1), 7.8 (t, 1), 8.05 (d, 1), 8.16 (d, 1), 8.95 (s, 1) ppm.

후처리

  1. customEvaporation

출처 및 근거

ORD 기록
ord-3e098c6c48fc44caa97e1ac101eb47dc
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995156B2

연결된 노트

불러오는 중…