Dimethylamine → HCID 21980634, compound

HRID 11135Notes

Reaction equation

HRID 11135 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.[CH3:33][NH:34][CH3:35].COC1C=CC2NC3C=C(C(OCC4C=CC=CC=4)=O)C4C(=O)NC(=O)C=4C=3C=2C=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:34]([CH3:35])[CH3:33])=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 11843434Benzyl 9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazole-4-carboxylateHCID 219809064-(2-Chlorophenyl)-8-(4-iodobutyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 21980634HCID 21980634, compoundYield 64%

Procedure

Reaction of the iodide (173) prepared as described in example 312 with aqueous dimethylamine using the procedure described in example 179 of Scheme 3 except that the reaction conditions were 6 h at room temperature gave (174) (64%) as an orange powder, mp 162–164° 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). EIMS found M+=475.1657, 477.1650. C27H26ClN3O3 requires 475.1663, 477.1633.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-ef93ac7314bc40abb94057164ba9666f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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