Nitrogen mustard hydrochloride → HCID 86663050, compound

HRID 2410808Notes

Reaction equation

HRID 2410808 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([Br:15])[CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:7]=3[NH:8][C:9]=2[CH:10]=1.Cl.Cl[CH2:22][CH2:23][N:24]([CH2:26][CH2:27]Cl)[CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>CC(O)(C)C>[Br:15][C:13]1[CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:7]2[NH:8][C:9]3[CH:10]=[C:2]([N:1]4[CH2:27][CH2:26][N:24]([CH3:25])[CH2:23][CH2:22]4)[CH:3]=[CH:4][C:5]=3[C:6]=2[N:14]=1

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 10340Sodium CarbonateHCID 86663051HCID 86663051, compound

Product 1

HCID 86663050HCID 86663050, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of methyl 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (1.0 g, 3.1 mmol), 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (1.20 g, 6.25 mmol) and sodium carbonate (1.66 g, 15 6 mmol) in t-BuOH (40 mL) was heated at reflux overnight. The reaction was partitioned between EtOAc and water and the organic phase was washed with sat. aq. NaHCO3 solution, water, and brine. After drying with sodium sulfate, the solvents were removed and silica gel chromatography (elution with 5% MeOH in DCM) afforded methyl 2-bromo-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (900 mg, 2.14 mmol, 69% yield). MS (ESI) m/z 405.14 (M+H); LCMS Ret Time: 1.995 min; Xbridge S10 4.6×50 mm column, 3 min gradient, 0-100% B, 4 mL/min. Solvent A: 95% MeOH—5% H2O—0.1% TFA; Solvent B: 5% MeOH—95% H2O—0.1% TFA.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe reaction was partitioned between EtOAc and water
  4. washthe organic phase was washed with sat. aq. NaHCO3 solution, water, and brine
  5. dry with materialAfter drying with sodium sulfate
  6. customthe solvents were removed
  7. washsilica gel chromatography (elution with 5% MeOH in DCM)

Sources & evidence

ORD record
ord-37ebc3d7021848cfbb638290b16ac197
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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