Dimethyl Sulfoxide → 6-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-beta-carboline

HRID 552181Notes

Reaction equation

HRID 552181 reaction equation
CS(C)=O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1F)[NH:15][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>O>[Cl:5][C:6]1[CH:7]=[C:8]2[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1[N:27]1[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]1)[NH:15][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole

Product 1

HCID 671656266-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-beta-carbolineYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMSO solution (4 ml) of 200 mg (0.755 mmol) of 6-chloro-7-fluoro-8-nitro-9H-β-carboline was added 1-methylpiperazine (226 mg, 2.26 mmol) and DIEA (400 mg, 3.09 mmol) via a syringe. The reaction was allowed to stir at RT overnight. Upon addition of water, an orange solid precipitated out. The solid was filtered, washed and dried to give 236 mg (91% yield) of the desired 6-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-β-carboline. 1H-NMR (300 MHz, DMSO-d6): δ 2.24 (s, 3H), 2.48 (m, 4H), 3.13 (m, 4H), 8.13 (d, 1H), 8.40 (d, 1H), 8.73 (s, 1H), 8.94 (s, 1H), 12.05 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.72 min. MS (M+H+): 346.

Workup

  1. customan orange solid precipitated out
  2. filtrationThe solid was filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-6458a34e1c0c41f2a3e55ef0ee0e72a2
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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