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

HRID 11111

Reaction equation

HRID 11111 reaction equation
[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][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]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][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[O:30])[C:10]=2[CH:9]=1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 4082852-MorpholinoethylamineHCID 103428973-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1h)-yl)propanoic acid

Product 1

HCID 914862873-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(4-morpholinyl)ethyl]propanamideYield 73%

Procedure

Reaction of acid (117) prepared as described in example 230 with oxalyl chloride followed by N-(2-aminoethyl)morpholine using the procedure described in example 207 gave the amide (120) (73%) as a yellow powder, mp 174–176° C. 1H NMR δ [(CD3)2SO] 11.12 (br s, 1H), 8.51 (d, J=2.6 Hz, 1H), 7.77 (s, 1H), 7.74 (t, J=5.6 Hz, 1H), 7.68 (d, J=9.0 Hz, 1H), 7.58 (m, 1H), 7.53–7.44 (m, 3H), 7.31 (dd, J=9.0, 2.6 Hz, 1H), 4.71 (t, J=6.3 Hz, 2H), 3.90 (s, 3H), 3.40 (t, J=4.6 Hz, 4H), 2.97 (m, 1H), 2.58 (t, J=6.3 Hz, 2H), 2.11 (br t, J=4.6 Hz, 4H), 2.00 (t, J=6.7 Hz, 2H). Found: C, 60.46; H, 5.26; N, 9.27. C30H29ClN4O5.2H2O requires C, 60.35; H, 5.94; N, 9.38.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-ebf2c83b161a4451bd0502da9dbb9704
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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