N,N-Dimethylethylenediamine → HCID 59813825, compound

HRID 1925287Notes

Reaction equation

HRID 1925287 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 24822603HCID 24822603, compound

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-d7a09079aaf44c70aa400071e5cbae36
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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