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1,2-Dimethoxyethane → N-{[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methyl}-5-methyl-3-isoxazolecarboxamide

HRID 992578
ノート
印刷プレビュー

反応式

HRID 992578 の反応式
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7](Cl)=[O:8])[CH:3]=1.[Cl:10][C:11]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:12]=1[CH2:13][N:14]1[C:26]2[CH:25]=[N:24][C:23]([CH2:27][NH2:28])=[CH:22][C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2.COCCOC.C(N(CC)CC)C>ClCCCl>[Cl:10][C:11]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:12]=1[CH2:13][N:14]1[C:26]2[CH:25]=[N:24][C:23]([CH2:27][NH:28][C:7]([C:4]3[CH:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[O:8])=[CH:22][C:21]=2[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 80711,2-Dimethoxyethane2 回HCID 8471TriethylamineHCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 9798774[9-(2,5-dichlorobenzyl)-9H-beta-carbolin-3-yl]methylamine

生成物 1

HCID 9825731N-{[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methyl}-5-methyl-3-isoxazolecarboxamide

試薬・触媒・溶媒 1

HCID 11
1,2-Dichloroethane
溶媒

実験手順

A solution of 5-methylisoxazole-3-carbonyl chloride in DCE (0.25M) was treated with a solution of [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methylamine in DME (0.25M, 1 equiv), followed by a solution of triethylamine in DME (1.0M, 1 equiv). The mixture was agitated, and allowed to stand overnight. The solvent was evaporated and the residue purified by preparative HPLC. 1H NMR (300 MHz, DMSO-d6) δ9.5 (br t, 1H), 9.40 (s, 1H), 8.74 (s, 1H), 8.60 (d,J=7.8 Hz, 1H) 7.78 (m, 1H), 7.66-7.60 (m, overlap, 2H), 7.50-7.41 (m, overlap, 2H), 6.69 (s, 1H), 6.65 (s, 1H), 5.97 (s, 1H), 4.96 (d, J=5.4Hz, 2H), 2.49 (s, overlap with DMSO peak). A peak at 13.7 ppm in the 13C NMR spectrum is consistent with the methyl group, which presumably overlaps with the solvent in the 1H NMR spectrum. Monoisotopic mass calcd for C24H18Cl2N4O2: 464.1, (M+H) found 465.4.

後処理

  1. customThe solvent was evaporated
  2. customthe residue purified by preparative HPLC

出典と根拠

ORDレコード
ord-d553ad7b374147bc818e990f6085f222
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06469021B1

反応ノート

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