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

HRID 992578Notes

Reaction equation

HRID 992578 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d553ad7b374147bc818e990f6085f222
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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