Imidazole → 6-(2-(1H-imidazol-1-yl)ethyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11093Notes

Reaction equation

HRID 11093 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]3[C:27](=[O:31])[NH:28][C:29](=[O:30])[C:16]=3[C:15]=2[C:14]2[CH:13]=[C:12]([OH:32])[CH:11]=[CH:10][C:9]1=2)(=O)=O.[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1>>[OH:32][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:7][CH2:6][N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)[C:20]3[CH:19]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:17]4[C:27](=[O:31])[NH:28][C:29](=[O:30])[C:16]=4[C:15]=3[C:14]=2[CH:13]=1

Participants

3

Reactant 2

HCID 795ImidazoleHCID 867602022-(9-Hydroxy-1,3-dioxo-4-phenyl-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate

Product 1

HCID 219807286-(2-(1H-imidazol-1-yl)ethyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 50%

Procedure

Mesylate (205) (70 mg, 0.16 mmol) prepared as described in example 174 was reacted with imidazole according to the procedure described in example 179 to give amine (213) (34 mg, 50%) as a yellow powder, mp>345° C. 1H NMR δ [(CD3)2SO] 11.05 (br s, 1H), 9.34 (s, 1H), 8.39 (d, J=2.4 Hz, 1H), 7.59 (m, 2H), 7.45 (m, 5H), 7.27 (s, 1H), 7.06 (dd, J=8.8, 2.4 Hz, 1H), 7.02 (s, 1H), 6.75 (s, 1H), 4.80 (t, J=5.7 Hz, 2H), 4.41 (t, J=5.7 Hz, 2H). Found: C, 70.36; H, 4.38; N, 12.68. C25H18N4O3.1/4H2O requires: C, 70.33; H, 4.37; N, 13.12.

Sources & evidence

ORD record
ord-30442443bd474eb2884df4fb92dcbd48
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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