Potassium Carbonate → 4-Methoxyquinoline-2-carboxamide

HRID 348086

反応式

HRID 348086 の反応式
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+]>CN(C=O)C.N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>[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]

参加物

5

反応物 2

HCID 11430Potassium CarbonateHCID 178473365HCID 178473365、化合物

生成物 1

HCID 149256254-Methoxyquinoline-2-carboxamide収率 88.3%

試薬・触媒・溶媒 2

HCID 1859152-Naphthylalanine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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), Nal (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), 8.95 (s, 1) ppm.

後処理

  1. customEvaporation

出典と根拠

ORDレコード
ord-07764897b3a34ffbbd641032ece737ec
出典データセット
uspto-grants-2007_02
特許番号
US07176207B2

関連ノート

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