Ammonia → 3-(4-(2,6-Dichlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanamide

HRID 11103Notes

Reaction equation

HRID 11103 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][CH3:28])[CH:15]=[CH:14][C:13]=3[N:12]([CH2:29][CH2:30][C:31]([OH:33])=O)[C:11]=2[CH:10]=1.[NH3:34]>>[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][CH3:28])[CH:15]=[CH:14][C:13]=3[N:12]([CH2:29][CH2:30][C:31]([NH2:34])=[O:33])[C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 867602053-(4-(2,6-Dichlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanoic acid

Product 1

HCID 867602043-(4-(2,6-Dichlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanamideYield 73%

Procedure

Reaction of acid (244) (0.23 g, 0.48 mmol) prepared as described in example 204 according to the procedure described in example 207, except that concentrated ammonia (˜30%, 20 mL) was added as the amine, gave amide (250) (0.17 g, 73%) as a yellow powder, mp 261–264° C. 1H NMR δ [(CD3)2SO] 11.19 (br s, 1H), 8.50 (d, J=2.6 Hz, 1H), 7.87 (s, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.63 (m, 2H), 7.52 (dd, J=8.8, 7.3 Hz, 1H), 7.38 (br s, 1H), 7.33 (dd, J=9.0, 2.6 Hz, 1H), 6.87 (br s, 1H), 4.69 (t, J=6.7 Hz, 214), 3.91 (s, 3H), 2.57 (t, J=6.7 Hz, 2H). Found: C, 59.55; H, 3.79; N, 8.73. C14H17Cl2N3O4 requires: C, 59.75; H, 3.55; N, 8.71.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-b197a92233c64fc5a8d67b98bc499b20
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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