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

HRID 992578
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HRID 992578 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 80711,2-Dimethoxyethane2회HCID 8471TriethylamineHCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 9798774[9-(2,5-dichlorobenzyl)-9H-beta-carbolin-3-yl]methylamine

생성물 1

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

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d553ad7b374147bc818e990f6085f222
출처 데이터셋
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06469021B1

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