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

HRID 11092Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]3[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:29])[CH:8]=[CH:7][C:6]1=2.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>>[OH:29][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([CH2:4][CH2:3][CH2:2][N:30]3[CH:34]=[CH:33][N:32]=[CH:31]3)[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:14]4[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=4[C:12]=3[C:11]=2[CH:10]=1

Participants

Reactant 2

HCID 795Imidazole

HCID 867602016-(3-Bromopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 219806586-(3-(1H-imidazol-1-yl)propyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 53%

Procedure

Bromide (204) (80 mg, 0.18 mmol) prepared as described in example 173 was reacted with imidazole according to the procedure described in example 179 to give amine (212) (41 mg, 53%) as a yellow powder, mp 309–311° C. 1H NMR δ [(CD3)2SO] 11.06 (s, 1H), 9.36 (s, 1H), 8.40 (d, J=2.3 Hz, 1H), 7.69 (s, 1H), 7.64 (m, 3H), 7.47 (m, 4H), 7.22 (s, 1H), 7.14 (dd, J=8.8, 2.3 Hz, 1H), 6.89 (s, 1H), 4.44 (t, J=7.4 Hz, 2H), 4.07 (t, J=7.3 Hz, 2H), 2.24 (m, 2H). Found: C, 70.31; H, 4.78; N, 12.43. C26H20N4O3.1/2H2O requires: C, 70.10; H, 4.75; N, 12.57.

Sources & evidence

ORD record: ord-99f392333f6a419c98f8fcb3e8e152c6
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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