Tetrahydrofuran → 3-(4-(2,6-Dichlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1h)-yl)propanamide

HRID 11105Notes

Reaction equation

HRID 11105 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:21]2[C:22](=[O:26])[NH:23][C:24](=[O:25])[C:20]=2[C:19]2[C:18]3[CH:17]=[C:16]([O:27]C)[CH:15]=[CH:14][C:13]=3[N:12]([CH2:29][CH2:30][C:31]([NH2:33])=[O:32])[C:11]=2[CH:10]=1.O1CCCC1>C(OCC)(=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:21]2[C:22](=[O:26])[NH:23][C:24](=[O:25])[C:20]=2[C:19]2[C:18]3[CH:17]=[C:16]([OH:27])[CH:15]=[CH:14][C:13]=3[N:12]([CH2:29][CH2:30][C:31]([NH2:33])=[O:32])[C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 867602043-(4-(2,6-Dichlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanamide

Product 1

HCID 248849133-(4-(2,6-Dichlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1h)-yl)propanamideYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Reaction of methyl ether (250) (80 mg, 0.17 mmol)) prepared as described in example 210 according to The procedure described in example 80, followed by chromatography on silica eluting with ethyl acetate then tetrahydrofuran and trituration from ethyl acetate, gave amide (258) (47 mg, 59%) as an orange powder, mp 327–329° C. 1H NMR δ [(CD3)2SO] 11.12 (br s, 1H), 9.39 (s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.82 (s, 1H), 7.61 (m, 3H), 7.51 (dd, J=8.8, 7.4 Hz, 1H), 7.38 (br s, 1H), 7.15 (dd, J=8.9, 2.4 Hz, 1H), 6.87 (br s, 1H), 4.65 (t, J=6.7 Hz, 2H), 2.55 (t, J=6.7 Hz, 2H). Found: C, 57.75; H, 3.83; N, 8.50. C23H15Cl2N3O4.3/4H2O requires: C, 57.33; H, 3.45; N, 8.72.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-43b0467513d5487d801b433d3756f736
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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