N,N-Dimethylethylenediamine → HCID 59813825, compound

HRID 2115793Notes

Reaction equation

HRID 2115793 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26]([OH:28])=O)=[CH:21][CH:20]=[CH:19]2.Cl.CN(C)CCCN=C=NCC.C1C=NC2N(O)N=NC=2C=1.[CH3:51][N:52]([CH3:56])[CH2:53][CH2:54][NH2:55].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26]([NH:55][CH2:54][CH2:53][N:52]([CH3:56])[CH3:51])=[O:28])=[CH:21][CH:20]=[CH:19]2

Participants

7

Reactant 5

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 248226036-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoic acid

Product 1

HCID 59813825HCID 59813825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoic acid (80 mg, 0.213 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (61 mg, 0.32 mmol) and HOAT (29 mg, 0.213 mmol) were added to a reaction tube, then dissolved in DMF (0.6 mL). A solution of N,N-dimethylethylenediamine (23 mg, 0.256 mmol) in DMF (0.6 mL) was added to the reaction, followed by Hunig's base (75 mg, 0.581 mmol). The mixture became yellow and clear within 15 min and was stirred at RT for 16 h. The mixture was concentrated under vacuum. The remaining yellow oil was purified by silica gel chromatography (2% to 3% 7N NH3 in MeOH in CH2Cl2) to afford 6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-N-(2-(dimethylamino)ethyl)-1-naphthalenecarboxamide as a white solid. MS (ESI, pos. ion) m/z: 446.1 (M+1). Calc'd for C226H27N3O4-445.52.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customThe remaining yellow oil was purified by silica gel chromatography (2% to 3% 7N NH3 in MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-05ecf7fbff3f4a91b5e49afcda915ef9
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

Loading…