Sodium hydride → 2-(4-morpholinyl)ethyl 9-(3,5-dinitrobenzyl)-4-(methoxymethyl)-9H-beta-carboline-3-carboxylate

HRID 992572Notes

Reaction equation

HRID 992572 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH:7]=[N:6][C:5]=1[C:17]([O:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:18].[H-].[Na+].[N+:30]([C:33]1[CH:34]=[C:35]([CH:38]=[C:39]([N+:41]([O-:43])=[O:42])[CH:40]=1)[CH2:36]Cl)([O-:32])=[O:31]>CN(C=O)C>[N+:30]([C:33]1[CH:34]=[C:35]([CH:38]=[C:39]([N+:41]([O-:43])=[O:42])[CH:40]=1)[CH2:36][N:9]1[C:8]2[CH:7]=[N:6][C:5]([C:17]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:18])=[C:4]([CH2:3][O:2][CH3:1])[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 94673Benzene, 1-(chloromethyl)-3,5-dinitro-HCID 184122262-(4-morpholinyl)ethyl 4-(methoxymethyl)-9H-beta-carboline-3-carboxylate

Product 1

HCID 98075702-(4-morpholinyl)ethyl 9-(3,5-dinitrobenzyl)-4-(methoxymethyl)-9H-beta-carboline-3-carboxylateYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to Method A, using 2-(4-morpholinyl)ethyl 4-(methoxymethyl)-9H-β-carboline-3-carboxylate (100 mg, 0.27 mmol), sodium hydride (0.30 mmol, 12 mg of 60% mineral oil suspension), and 3,5-dinitrobenzyl chloride (65 mg, 0.30 mmol) in DMF (2 mL). Purification of the crude material by preparative thin layer chromatography with ethyl acetate/hexane (7:3) afforded 2-(4-morpholinyl)ethyl 9-(3,5-dinitrobenzyl)-4-(methoxymethyl)-9H-β-carboline-3-carboxylate (107 mg, 72%). 1H NMR (CDCl3) δ8.98 (s, 1H), 8.81 (s, 1H), 8.44 (d, J=8.0 Hz, 1H), 8.31 (d,J=1.9 Hz, 2H), 7.68 (t,J=7.3 Hz, 1H), 7.49 (t,J=7.6 Hz, 1H), 7.42 (d, J=8.3 Hz, 2H), 5.83 (s, 2H), 5.44 (s, 2H), 4.59 (t,J=5.8 Hz, 2H), 3.76 (t, J=4.5Hz, 4H), 3.56 (s, 3H), 2.85 (t,J=5.8Hz, 2H), 2.63 (t,J=4.5 Hz, 4H); MS (APCI; (M+H)+) m/z 550.

Workup

  1. customThe title compound was prepared
  2. customPurification of the crude material by preparative thin layer chromatography with ethyl acetate/hexane (7:3)

Sources & evidence

ORD record
ord-18a1ec973aeb438fbfa6da32a1a76de4
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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