Dimethylformamide → HCID 10579635, compound

HRID 1952873Notes

Reaction equation

HRID 1952873 reaction equation
[CH2:1]([C:3]1[CH:16]=[C:15]2[C:6]([N:7]=[C:8]3[C:13](=[CH:14]2)[CH:12]=[CH:11][CH:10]=[C:9]3[C:17](O)=[O:18])=[CH:5][CH:4]=1)[CH3:2].C1N=CN([C:25]([N:27]2[CH:31]=N[CH:29]=[CH:28]2)=O)C=1.C[N:33]([CH2:38][CH2:39][CH2:40]N)[CH2:34][CH2:35][CH2:36]N.[N-]1[CH:46]=[CH:45][N:44]=C1.[CH3:47][N:48]([CH:50]=[O:51])C>C1COCC1>[CH2:14]([C:15]1[CH:40]=[C:39]2[C:38]([N:33]=[C:34]3[C:35](=[CH:36]2)[CH:4]=[CH:3][CH:1]=[C:2]3[C:50]([NH:48][CH2:47][CH2:29][CH2:28][N:27]([CH2:31][CH2:46][CH2:45][NH:44][C:17]([C:9]2[C:8]3[C:13](=[CH:14][C:15]4[C:6]([N:7]=3)=[CH:5][CH:4]=[C:3]([CH2:1][CH3:2])[CH:16]=4)[CH:12]=[CH:11][CH:10]=2)=[O:18])[CH3:25])=[O:51])=[CH:5][CH:6]=1)[CH3:13]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 7777N,N-bis(3-aminopropyl)methylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 10610748HCID 10610748, compound

Product 1

HCID 10579635HCID 10579635, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above acridine acid (0.30 g, 1.2 mmol) was reacted with CDI (0.38 g, 2.39 mmol) in dry DMF (50 mL) for 4 h at 50° C. The DMF was removed under reduced pressure, and the resulting oil was dissolved in a mixture of petroleum ether and CH2Cl2 (20 mL, 3:1). Upon cooling, the imidazolide crystallized out and this crude material was used in the following coupling reaction. The coupling was carried out by dissolving 3,3'-diamino-N-methyldipropylamine (0.09 g) in THF (50 mL), cooling to 0° C. (ice/water), and adding the crude imidazolide portionwise. The reaction mixture was allowed to stir overnight at room temperature, the THF removed, and the residue diluted with CH2Cl2 (100 mL) which was subsequently washed with 1M Na2CO3 (50 mL). The CH2Cl2 layer was dried with Na2SO4, the solvent removed under reduced pressure, and the resulting brown oil purified by chromatography on alumina (0.5% MeOH in CH2Cl2 as eluant) to give bis[(7-ethylacridine-4-carboxamido)-propyl]methylamine (22) (0.17 g, 47%) as a yellow oil. 1H NMR (CDCl3) δ 1.28 (t, J=7.5 Hz, 6 H, 2×CH3), 2.03-2.11 (m, 4 H, 2×CH2CH2CH2), 2.40 (s, 3 H, NCH3), 2.70 (q, J=7.6 Hz, 4 H, 2×CH2CH3), 2.79 (t, J=7.4 Hz, 4 H, 2×CH2NCH3), 3.74 (q, J=6.2 Hz, 4 H, 2×CH2NH), 7.46 (br s, 2 H, H-8), 7.48 (dd, J=8.9, 1.8 Hz, 2 H, H-6), 7.56 (dd, J=8.3, 7.2 Hz, 2 H, H-2), 7.89 (d, J=8.8 Hz, 2 H, H-5), 7.98 (dd, J=8.3, 1.5 Hz, 2 H, H-1), 8.51 (s, 2 H, H-9), 8.86 (dd, J=7.1, 1.5 Hz, 2 H, H-3), 11.80 (br t, J=5.0 Hz, 2 H, CONH). HRMS. (FAB+) m/z calcd for C39H42N5O2 612.3339 (MH+), found 612.3333.

Workup

  1. customThe DMF was removed under reduced pressure
  2. dissolutionthe resulting oil was dissolved in a mixture of petroleum ether and CH2Cl2 (20 mL, 3:1)
  3. temperatureUpon cooling
  4. customthe imidazolide crystallized out
  5. customthis crude material was used in the following coupling reaction
  6. customthe THF removed
  7. additionthe residue diluted with CH2Cl2 (100 mL) which
  8. washwas subsequently washed with 1M Na2CO3 (50 mL)
  9. dry with materialThe CH2Cl2 layer was dried with Na2SO4
  10. customthe solvent removed under reduced pressure
  11. customthe resulting brown oil purified by chromatography on alumina (0.5% MeOH in CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-096b0e3c19f84fc1b2a176383d6416cd
Source dataset
uspto-grants-2000_09
Patent number
US06114332

Reaction notes

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