3-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)-n-[2-(dimethylamino)ethyl]propanamide → n-[2-(Dimethylamino)ethyl]-3-(9-hydroxy-4-(2-methoxyphenyl)-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)propanamide

HRID 11107Notes

Reaction equation

HRID 11107 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:29][CH2:30][C:31]([NH:33][CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])=[O:32])[C:12]=2[CH:11]=1>C(OCC)(=O)C.CO.[Pd]>[CH3:38][N:36]([CH3:37])[CH2:35][CH2:34][NH:33][C:31](=[O:32])[CH2:30][CH2:29][N:13]1[C:12]2[CH:11]=[C:10]([C:3]3[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=3[O:8][CH3:9])[C:22]3[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=3[C:20]=2[C:19]2[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]1=2

Participants

4

Reactant 1

HCID 117569303-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)-n-[2-(dimethylamino)ethyl]propanamide

Product 1

HCID 69583799n-[2-(Dimethylamino)ethyl]-3-(9-hydroxy-4-(2-methoxyphenyl)-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)propanamideYield 17.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of amide (260) (40 mg, 0.07 mmol)) prepared as described in example 219 in ethyl acetate/methanol (1:1, 80 mL) was added 5% Pd-C (catalytic). The resulting suspension was hydrogenated at 60 psi with stirring for 4 days, with additional portions of Pd-C being added every 24 hours. The reaction mixture was then filtered through celite and concentrated under reduced pressure before being chromatographed on silica eluting with methanol/ethyl acetate/triethylamine (1:4:trace), to give amide (330) (6 mg, 16%) as a yellow powder, mp 232–238° C. 1H NMR δ [(CD3)2SO] 10.95 (br s, 1H), 9.33 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 8.01 (br s, 1H), 7.69 (s, 1H), 7.54 (d, J=8.9 Hz, 1H), 7.43 (m, 1H), 7.34 (dd, J=7.5, 1.8 Hz, 1H), 7.13–7.05 (m, 3H), 4.67 (t, J=6.2 Hz, 2H), 3.69 (s, 3H), −3.2 (obscured m, 2H), 2.60 (t, J=6.2 Hz, 2H), 2.54–2.49 (obscured m, 8H). FABMS found [M+H]+: 501.2142. C28H28N4O5 requires 501.2138.

Workup

  1. additionadded every 24 hours
  2. filtrationThe reaction mixture was then filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. custombefore being chromatographed on silica eluting with methanol/ethyl acetate/triethylamine (1:4:trace)

Sources & evidence

ORD record
ord-2d72889ef0374e16a7cf146871cfef15
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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