Pyrrolidine → 4-(2-Chlorophenyl)-9-methoxy-8-[4-(1-pyrrolidinyl)butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11136Notes

Reaction equation

HRID 11136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26][CH3:27])[C:14]([CH2:28][CH2:29][CH2:30][CH2:31]I)=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26][CH3:27])[C:14]([CH2:28][CH2:29][CH2:30][CH2:31][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 219809064-(2-Chlorophenyl)-8-(4-iodobutyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 219807984-(2-Chlorophenyl)-9-methoxy-8-[4-(1-pyrrolidinyl)butyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 75%

Procedure

Reaction of the iodide (173) prepared as described in example 312 with pyrrolidine using the procedure described in example 179 except that the reaction conditions were 2 h at room temperature gave (176) (75%) as an orange powder, which was used without further purification, mp 173–178° C. 1H NMR δ [(CD3)2SO] 11.85 (s, 1H), 11.04 (br s, 1H), 8.42 (s, 1H), 7.57 (dd, J=8.0, 2.2 Hz, 1H), 7.55 (s, 1H), 7.51–7.43 (m, 3H), 7.42 (s, 1H), 3.93 (s, 3H), 2.77 (t, J=7.4 Hz, 2H), 2.24 (t, J=7.3 Hz, 2H), 2.11 (s, 6H), 1.63 (m, 2H), 1.47 (m, 2H).

Workup

  1. customprepared
  2. customdescribed in example 179 except that the reaction conditions

Sources & evidence

ORD record
ord-53b8de3adf874b74b5aac8d0effc825e
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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