N,N-Dimethylethylenediamine → Pyrido[4,3-a]phenazine-11-carboxamide, N-[2-(dimethylamino)ethyl]-

HRID 1267010Notes

Reaction equation

[CH:1]1[C:6]2=[C:7]3[C:16](=[CH:17][CH:18]=[C:5]2[CH:4]=[N:3][CH:2]=1)[N:15]=[C:14]1[C:9]([C:10]([C:19]([OH:21])=O)=[CH:11][CH:12]=[CH:13]1)=[N:8]3.[CH:22]1[N:26]=[CH:25][N:24]([C:27](N2C=NC=C2)=O)[CH:23]=1.CN(C)CCN>CN(C=O)C>[CH3:25][N:24]([CH3:27])[CH2:23][CH2:22][NH:26][C:19]([C:10]1[C:9]2[C:14](=[N:15][C:16]3[C:7]([N:8]=2)=[C:6]2[CH:1]=[CH:2][N:3]=[CH:4][C:5]2=[CH:18][CH:17]=3)[CH:13]=[CH:12][CH:11]=1)=[O:21]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of pyrido[4,3-α]phenazine-11-carboxylic acid (II.3) (0.11 g, 0.38 mmol) and CDI (0.12 g, 0.76 mmol) in DMF (5 mL) was heated and stirred at 50-60° C. for 2 h. N,N-Dimethylethylenediamine (0.5 mL, excess) was then added, and the mixture was stirred at room temperature for 2 h. The DMF was removed under reduced pressure, and the residue was diluted with water. The resulting precipitate was collected and crystallized from CH2Cl2/hexane to give pyrido[4,3-α]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (0.11 g, 84%): mp 213-215° C.; 1H NMR [CDCl3] δ 2.48 [s, 6 H, N(CH3)2], 2.75 [t, J=5.7 Hz, 2 H, CH2N(CH3)2], 3.89 (q, J=5.5 Hz, 2 H, CH2NH), 8.03-8.14 (m, 3 H, 3xArH), 8.42 (dd, J=8.4, 1.5 Hz, 1 H, ArH), 9.00 (d, J=5.5 Hz, 1 H, H-1 or H-2), 9.07 (dd, J=7.2, 1.5 Hz, 1 H, H-10), 9.34 (s, 1 H, H-4), 9.36 (d, J=5.5 Hz, 1 H, H-1 or H-2), 10.66 (br, 1 H, CONH).

Workup

temperaturewas heated
stirringthe mixture was stirred at room temperature for 2 h
customThe DMF was removed under reduced pressure
additionthe residue was diluted with water
customThe resulting precipitate was collected
customcrystallized from CH2Cl2/hexane

Sources & evidence

ORD record: ord-57824e798ca548419ea421fe59c69369
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552021B2

Reaction notes

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