rel-(2R,6S)-2,6-dimethylpiperazine → 4-(2-Chloro-6-methoxyphenyl)-6-{3-[cis-3,5-dimethylpiperazinyl]propyl}-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11097Notes

Reaction equation

HRID 11097 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:26])[C:14]3[C:27](=[O:31])[NH:28][C:29](=[O:30])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:32])[CH:8]=[CH:7][C:6]1=2.[CH3:33][C@H:34]1[CH2:39][NH:38][CH2:37][C@@H:36]([CH3:40])[NH:35]1>>[Cl:26][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([O:24][CH3:25])[C:18]=1[C:15]1[C:14]2[C:27](=[O:31])[NH:28][C:29](=[O:30])[C:13]=2[C:12]2[C:11]3[CH:10]=[C:9]([OH:32])[CH:8]=[CH:7][C:6]=3[N:5]([CH2:4][CH2:3][CH2:2][N:38]3[CH2:37][C@H:36]([CH3:40])[NH:35][C@H:34]([CH3:33])[CH2:39]3)[C:17]=2[CH:16]=1

Participants

3

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 104364886-(3-Bromopropyl)-4-(2-chloro-6-methoxyphenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 695839064-(2-Chloro-6-methoxyphenyl)-6-{3-[cis-3,5-dimethylpiperazinyl]propyl}-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 98%

Procedure

Bromide (207) (60 mg, 0.12 mmol), prepared as described in example 176, was reacted with cis-2,6-dimethylpiperazine according to the procedure described in example 179 except that the reaction was performed at room temperature for 20 h, to give amine (218) (63 mg, 98%) as a yellow powder, mp 199–202° C. 1H NMR δ [(CD3)2SO] 10.99 (br s, 1H), 9.37 (br s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.75 (s, 1H), 7.57 (d, J=8.8 Hz, 1H), 7.43 (t, J=8.2 Hz, 1H), 7.15 (m, 3H), 4.45 (t, J=6.1 Hz, 2H), 3.67 (s, 3H), 2.49 (m, 4H), 2.11 (m, 2H), 1.90 (m, 2H), 1.27 (m, 2H), 0.79 (m, 6H). Found: C, 61.35; H, 5.68; N, 9.14. C30H31ClN4O4.2¼H2O requires: C, 61.32; H, 6.09; N, 9.54.

Sources & evidence

ORD record
ord-3891d5b333be4fc9af36bb80c85af3c7
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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