1-Hydroxybenzotriazole → 2,3-Dihydrobenzofuran-7-carboxylic acid methyl-(2-{[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]pyridin-4-ylmethylamino}ethyl)amide dihydrochloride

HRID 69010

反応式

HRID 69010 の反応式
N=C=N.ON1C2C=CC=CC=2N=N1.[CH3:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:37][CH2:38][NH:39][CH3:40])[CH2:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]1=[O:41].[O:42]1[C:46]2[C:47]([C:51](O)=[O:52])=[CH:48][CH:49]=[CH:50][C:45]=2[CH2:44][CH2:43]1.C(OC(=O)C)C.[ClH:60]>C(OCC)(=O)C.C1COCC1.C(#N)C>[ClH:60].[ClH:60].[CH3:40][N:39]([CH2:38][CH2:37][N:29]([CH2:28][CH2:27][CH2:26][O:25][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:15]([CH3:14])[C:16](=[O:41])[CH:17]=[CH:18]2)[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)[C:51]([C:47]1[C:46]2[O:42][CH2:43][CH2:44][C:45]=2[CH:50]=[CH:49][CH:48]=1)=[O:52]

参加物

9

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acidHCID 21866389Hydrogen chloride-ethyl acetateHCID 669605791-Methyl-6-{3-[(2-methylamino-ethyl)-pyridin-4-ylmethyl-amino]-propoxy}-1H-quinolin-2-one

生成物 1

HCID 706571802,3-Dihydrobenzofuran-7-carboxylic acid methyl-(2-{[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]pyridin-4-ylmethylamino}ethyl)amide dihydrochloride

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

PS-Carbodiimide resin (1.3 g) and 1-hydroxy benzotriazole (HOBt) (230 mg) were added to acetonitrile and THF solution (4 ml+6 ml) of 1-methyl-6-{3-[(2-methylaminoethyl)pyridin-4-ylmethylamino]propoxy}-1H-quinolin-2-one (304 mg) and 2,3-dihydrobenzofuran-7-carboxylic acid (164 mg). The mixture was stirred at room temperature overnight. After the reaction mixture was filtrated and condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.35 ml) was added to an ethyl acetate solution of the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (324.2 mg) as a white powder.

後処理

  1. filtrationAfter the reaction mixture was filtrated
  2. customcondensed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1)
  4. customcondensed under reduced pressure
  5. customThe precipitated insoluble matter was separated
  6. washwashed with ethyl acetate
  7. customdried

出典と根拠

ORDレコード
ord-56afdde03ef94cfaa7f0355ac72a4f1a
出典データセット
uspto-grants-2014_09
特許番号
US08822453B2

関連ノート

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