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 11107노트

반응식

HRID 11107 반응식
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

참가 물질

4

반응물 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

생성물 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)propanamide수율 17.1%

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 21584119Ethylacetate methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2d72889ef0374e16a7cf146871cfef15
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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