Nitrogen mustard hydrochloride → HCID 18622550, compound

HRID 427343Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[C:21]([NH2:30])[CH:22]=[CH:23][C:24]=3[O:28][CH3:29])[CH2:19]2)=[O:17])=[O:8])[CH2:3][CH2:2]1.Cl.Cl[CH2:33][CH2:34][N:35]([CH2:37][CH2:38]Cl)[CH3:36].C(=O)([O-])O.[Na+].[OH-].[NH4+]>C(O)CCC>[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[C:21]([N:30]4[CH2:38][CH2:37][N:35]([CH3:36])[CH2:34][CH2:33]4)[CH:22]=[CH:23][C:24]=3[O:28][CH3:29])[CH2:19]2)=[O:17])=[O:8])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of N-(morpholinocarbonylphenyl)-8-amino-5-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide (280 mg, 0.69 mmol), bis(2-chloroethyl)methyl amine hydrochloride (190 mg, 1.0 mmol) and sodium hydrogen carbonate (84 mg, 1.0 mmol) in n-butanol (20 mL) was heated at 90° C. for 5 h. After cooling, 2 M ammonium hydroxide (10 mL) was added and the mixture was heated at 50° C. for 1 h. The organic phase was evaporated in vacuo and the residue was purified by flash chromatography on a 5 silica gel column using chloroform/ethanol/conc. ammonium hydroxide (90:10:0.5) as eluent to yield 60 mg (18%) of the title compound: EIMS (70 eV) m/z (relative intensity) 492 (50, M+).

Workup

temperatureAfter cooling
customThe organic phase was evaporated in vacuo
customthe residue was purified by flash chromatography on a 5 silica gel column

Sources & evidence

ORD record: ord-914a6e114dcd4eb185ced59f5a4392f2
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313118B1

Reaction notes

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