1-Hydroxybenzotriazole → (E)-3-(6-acetamidopyridin-3-yl)-N-[2-[2,4-dichloro-N-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]prop-2-enamide

HRID 1635600ノート

反応式

HRID 1635600 の反応式
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[CH:17]2)[CH3:6])=[O:4].[C:28]([NH:31][C:32]1[N:37]=[CH:36][C:35](/[CH:38]=[CH:39]/[C:40](O)=[O:41])=[CH:34][CH:33]=1)(=[O:30])[CH3:29].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[C:28]([NH:31][C:32]1[N:37]=[CH:36][C:35](/[CH:38]=[CH:39]/[C:40]([NH:1][CH2:2][C:3]([N:5]([C:7]2[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=2)[CH2:10][O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[C:19]([CH3:22])[CH:18]=[CH:17]3)[CH3:6])=[O:4])=[O:41])=[CH:34][CH:33]=1)(=[O:30])[CH3:29]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10703461(E)-3-(6-Acetamidopyridin-3-YL)acrylic acidHCID 117954848-[3-(N-glycyl-N-methylamino)2,6-dichlorobenzyloxy]-2-methylquinoline

生成物 1

HCID 5311108(E)-3-(6-acetamidopyridin-3-yl)-N-[2-[2,4-dichloro-N-methyl-3-[(2-methylquinolin-8-yl)oxymethyl]anilino]-2-oxoethyl]prop-2-enamide収率 53.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylquinoline (100 mg), (E)-3-(6-acetamidopyridin-3-yl)acrylic acid (56.1 mg) and N,N-dimethylformamide (2 ml) were added 1-hydroxy-benzotriazole (43.4 mg) and 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride (56.9 mg) in a nitrogen stream at 0° C., and the resulting mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into water, and extracted with chloroform. The organic layer was washed with an aqueous solution of saturated sodium hydrogencarbonate, water and brine successively, and dried over magnesium sulfate, and thereafter the solvent was removed under reduced pressure. The residue was purified by preparative thin-layer chromatography (methanol:dichloromethane=1:10, v/v), and solidified with diethyl ether and ethyl acetate to give 8-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloyl-glycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methyl-quinoline (FR173657) (78.8 mg) as a grayish white solid.

後処理

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with an aqueous solution of saturated sodium hydrogencarbonate, water and brine successively
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative thin-layer chromatography (methanol

出典と根拠

ORDレコード
ord-246468920e4a40358f9080d502dabd02
出典データセット
uspto-grants-2003_01
特許番号
US06509468B1

反応ノート

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