Ammonia → HCID 22464183, compound

HRID 1934822Notes

Reaction equation

HRID 1934822 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:21][C:20]4[C:22]([NH2:28])=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:19]=4[O:18][CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl.Cl[CH2:31][CH2:32][N:33]([CH2:35][CH2:36]Cl)[CH3:34].C(=O)([O-])O.[Na+].N>C(O)CCC>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:21][C:20]4[C:22]([N:28]5[CH2:36][CH2:35][N:33]([CH3:34])[CH2:32][CH2:31]5)=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:19]=4[O:18][CH2:17]3)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 5935Nitrogen mustard hydrochlorideHCID 516892Sodium BicarbonateHCID 22464174HCID 22464174, compound

Product 1

HCID 22464183HCID 22464183, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of N-(4-morpholinophenyl)-5-amino-8-methoxy-3,4-dihydro-2H-1-benzopyran-3-carboxamide (270 mg, 0.7 mmol), bis (2-chloroethyl)-methylamine hydrochloride (288 mg, 1.5 mmol) and sodium hydrogen carbonate (126 mg, 1.5 mmol) in n-butanol (10 mL) was stirred at 90° C. for 2.5 h. 2 M ammonia (10 mL) was added at 50° C., the mixture was cooled and the phases were separated. The organic phase evaporated in vacuo and the residue was purified by column chromatography on silica gel using ethyl acetate/triethyl amine (100:8) as the eluent affording 170 mg (50% yield) of the title compound as white crystals: mp 202-204° C.; EIMS (70 eV) m/z (relative intensity) 466 (100 M+).

Workup

  1. temperaturethe mixture was cooled
  2. customthe phases were separated
  3. customThe organic phase evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d74da61990864a449a78fe890cf95252
Source dataset
uspto-grants-2002_05
Patent number
US06384225B1

Reaction notes

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