Nitrogen mustard hydrochloride → 3-bromo-7-(4-methylpiperazin-1-yl)-9H-carbazole-1-carboxamide

HRID 2410912Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[C:8]([Br:18])[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.Cl.Cl[CH2:21][CH2:22][N:23]([CH2:25][CH2:26]Cl)[CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>CC(O)(C)C>[Br:18][C:8]1[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]2[NH:12][C:13]3[C:5]([C:6]=2[CH:7]=1)=[CH:4][CH:3]=[C:2]([N:1]1[CH2:26][CH2:25][N:23]([CH3:24])[CH2:22][CH2:21]1)[CH:14]=3

Participants

Conditions

Temperature: 80 °C

Procedure

7-Amino-3-bromo-9H-carbazole-1-carboxamide 470B (250 mg, 0.822 mmol), 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride, Mechlorethamine HCl (316 mg, 1.644 mmol) and sodium carbonate (436 mg, 4.11 mmol) were mixed in t-BuOH (5 mL) in a sealed microwave vial. The vial was degassed and filled with N2. The mixture was heated at 80° C. for 16 hrs in an oil bath. 6 ml of DMF was added to the mixture and the mixture was heated in microwave at 160° C. for 1 hr. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 387.04 (M+H)+.

Workup

customThe vial was degassed
additionfilled with N2
addition6 ml of DMF was added to the mixture
temperaturethe mixture was heated in microwave at 160° C. for 1 hr
concentrationThe mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-0abd47c00ffe4e49925a53390979ef7f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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