6-(3-(1H-imidazol-1-yl)propyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione → 3-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)-n-[2-(dimethylamino)ethyl]propanamide

HRID 11106Notes

Reaction equation

HRID 11106 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([O:28]C)[CH:16]=[CH:15][C:14]=3[N:13]([CH2:30][CH2:31][C:32]([NH:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[O:33])[C:12]=2[CH:11]=1.OC1C=CC2N(CCCN3C=CN=C3)C3C=C(C4C=CC=CC=4)C4C(=O)NC(=O)C=4C=3C=2C=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:30][CH2:31][C:32]([NH:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[O:33])[C:12]=2[CH:11]=1

Participants

3

Reactant 2

HCID 219806586-(3-(1H-imidazol-1-yl)propyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 91312222HCID 91312222, compound

Product 1

HCID 117569303-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)-n-[2-(dimethylamino)ethyl]propanamideYield 83%

Procedure

Reaction of methyl ether (252) prepared as described in example 212 (80 mg, 0.15 mmol) according to The procedure described in example 80, except that the reaction was performed at 0° C. for 2 hours and chromatography was performed eluting with ethyl acetate/methanol/triethylamine (1:0:0 to 3:1:trace), gave amide (260) (65 mg, 83%) as a yellow/orange powder, mp 200–205° C. 1H NMR δ [(CD3)2SO] 11.00 (br s, 1H), 9.34 (s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.87 (br s, 1H), 7.66 (s, 1H), 7.54 (d, J=8.9 Hz, 1H), 7.44 (t, J=8.2 Hz, 1H), 7.18 (dd, J=8.2, 0.7 Hz, 1H), 7.12 (m, 2H), 4.64 (t, J=6.6 Hz, 2H), 3.68 (s, 3H), 3.05 (m, 2H), 2.56 (t, J=6.6 Hz, 2H), 2.23 (v br s, 2H), 2.15 (br s, 6H). Found: C, 58.98; H, 5.12; N, 9.59. C28H27ClN4O5.2H2O requires: C, 58.90; H, 5.47; N, 9.81.

Workup

  1. customprepared
  2. washchromatography was performed eluting with ethyl acetate/methanol/triethylamine (1:0:0 to 3:1:trace)

Sources & evidence

ORD record
ord-66d5617ee3174b04900152f40608af0f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

Loading…