Oxalyl chloride → 3-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamide

HRID 11117

Reaktionsgleichung

Reaktionsgleichung von HRID 11117
[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]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29](O)=[O:30])[C:10]=2[CH:9]=1.[C:32](Cl)(=O)C(Cl)=O.[NH2:38][CH2:39][CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=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][CH3:32])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29]([NH:38][CH2:39][CH2:40][C:41]3[NH:45][CH:44]=[N:43][CH:42]=3)=[O:30])[C:10]=2[CH:9]=1

Komponenten

4

Edukt 3

HCID 65578Oxalyl chlorideHCID 103428973-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1h)-yl)propanoic acidHCID 178419017HCID 178419017, Verbindung

Produkt 1

HCID 867602123-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamideAusbeute 81 %

Versuchsvorschrift

Reaction of acid (117) prepared as described in example 230 with oxalyl chloride followed by histamine using the procedure described in example 207 gave the amide (128) (81%) as a yellow powder, mp 144–149° C. (dec). 1H NMR δ [(CD3)2SO] 11.12 (br, 1H), 8.52 (d, J=2.6 Hz, 1H), 7.91 (t, J=5.5 Hz, 1H), 7.76 (s, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.58 (m, 1H), 7.52–7.42 (m, 4H), 7.32 (dd, J=9.0, 2.6 Hz, 1H), 6.56 (s, 1H), 4.69 (t, J=6.4 Hz, 2H), 3.90 (s, 3H), 3.12 (m, 2H), 2.58 (t, J=6.4 Hz, 2H), 2.39 (t, J=7.4 Hz, 2H). Found: C, 60.73; H, 4.49; N, 11.49. C29H24ClN5O4. 1/2CH2Cl2 requires C, 60.62; H, 4.31; N, 11.98.

Aufarbeitung

  1. customprepared

Quellen und Nachweise

ORD-Eintrag
ord-433c46922dbe4aab9fda6d1573802cf3
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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