Morpholine → 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-[2-(4-morpholinyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11057Notes

Reaction equation

HRID 11057 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[C:18]([C:21]3[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:29])[C:17]3[C:30](=[O:34])[NH:31][C:32](=[O:33])[C:16]=3[C:15]=2[C:14]2[CH:13]=[C:12]([OH:35])[CH:11]=[CH:10][C:9]1=2)(=O)=O.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.COC1C=CC2NC3C=C(C(OCC4C=CC=CC=4)=O)C4C(=O)NC(=O)C=4C=3C=2C=1>>[Cl:29][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:21]=1[C:18]1[C:17]2[C:30](=[O:34])[NH:31][C:32](=[O:33])[C:16]=2[C:15]2[C:14]3[CH:13]=[C:12]([OH:35])[CH:11]=[CH:10][C:9]=3[N:8]([CH2:7][CH2:6][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[C:20]=2[CH:19]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 11843434Benzyl 9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazole-4-carboxylateHCID 867601972-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate

Product 1

HCID 219804724-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-[2-(4-morpholinyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 81%

Procedure

Reaction of 2-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate (VII; Ar=2-chloro-6-methoxyphenyl, n=2, mesylate) (114) prepared as described in example 66 with morpholine using the procedure described in example 179 of Scheme 3 gave 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-[2-(4-morpholinyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VIII; Ar=2-chloro-6-methoxyphenyl, n=2, Z=4-morpholinyl) (115) in an 81% yield as a yellow powder; mp 185° C. 1H NMR δ [(CD3)2SO] 10.99 (br s, 1H), 9.34 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.69 (s, 1H), 7.57 (d, J=8.8 Hz, 1H), 7.44 (dd, J=8.3, 8.3 Hz, 1H), 7.17 (d, J=8.3 Hz, 1H), 7.14–7.10 (m, 2H), 4.53 (t, J=6.1 Hz, 2H), 3.66 (s, 3H), 3.41 (t, J=4.5 Hz, 4H), 2.64 (t, J=6.1 Hz, 2H), 2.37 (m, 4H). Found: C, 63.57; H, 4.71; N, 8.06. C27H24ClN3O5.1/4H2O requires C, 63.53; H, 4.84; N, 8.23.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-915b6fcb2b644f1a8f05948a5bd18cc0
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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