2-Chloronicotinic acid → 2-chloro-N-[6-chloro-7-(4-methyl-piperazin-1-yl)-9H-beta-carbolin-8-yl]-nicotinamide

HRID 552183Notes

Reaction equation

HRID 552183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:22])[C:14]=1[N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[Cl:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](O)=[O:27].C([O-])(=O)C.[NH4+]>>[Cl:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH:22][C:13]1[C:14]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[C:2]([Cl:1])[CH:3]=[C:4]2[C:12]=1[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1)=[O:27]

Participants

4

Reactant 3

HCID 762582-Chloronicotinic acidHCID 517165Ammonium AcetateHCID 671667376-chloro-7-(4-methyl-piperazin-1-yl)-8-amino-9H-beta-carboline

Product 1

HCID 113400222-chloro-N-[6-chloro-7-(4-methyl-piperazin-1-yl)-9H-beta-carbolin-8-yl]-nicotinamideYield 25%

Procedure

The desired compound was prepared according to Method A from 6-chloro-7-(4-methyl-piperazin-1-yl)-8-amino-9H-β-carboline and 2-chloro-nicotinic acid in 25% yield. 1H-NMR (300 MHz, DMSO-d6): δ 2.21 (s, 3H), 2.33 (m, 2H), 2.54(m, 2H), 3.24 (m, 4H), 7.73 (dd, 1H), 8.12 (d, 1H), 8.35 (d, 1H), 8.37 (s, 1H), 8.48 (dd, 1H), 8.61 (dd, 1H), 8.91 (s, 1H), 10.40 (s, 1H), 11.33 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.46 min. MS (M+H+): 455.

Workup

  1. custom1.46 min

Sources & evidence

ORD record
ord-fb30e4c47fa64382bb80c8ab9b9ba316
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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