Phosphorus tribromide → 8-(1-bromoethyl)-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide

HRID 1187190Notes

Reaction equation

HRID 1187190 reaction equation
[Br:1]P(Br)Br.[CH3:5][N:6]([CH3:32])[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[C:14]2[C:19](=[C:20]([CH:22](O)[CH3:23])[CH:21]=1)[O:18][C:17]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[CH:16][C:15]2=[O:31])=[O:11]>C(Cl)Cl>[BrH:1].[Br:1][CH:22]([C:20]1[CH:21]=[C:12]([C:10]([NH:9][CH2:8][CH2:7][N:6]([CH3:32])[CH3:5])=[O:11])[CH:13]=[C:14]2[C:19]=1[O:18][C:17]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[CH:16][C:15]2=[O:31])[CH3:23]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 58235055N-(2-(dimethylamino)ethyl)-8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Product 1

HCID 671039198-(1-bromoethyl)-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of tribromophosphine 1M in DCM (0.154 mL, 0.15 mmol) at 25° C., was added dropwise to N-(2-(dimethylamino)ethyl)-8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide (60 mg, 0.15 mmol) suspended in DCM (1 mL). This suspension was stirred at 25° C. for 4 days. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to afford 8-(1-bromoethyl)-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (98 mg, >100%) as a white solid, which was used without further purification. Mass Spectrum: M+H+ 454.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-5d6b449cb9964b52b25d0f04b3eebc81
Source dataset
uspto-grants-2014_03
Patent number
US08673906B2

Reaction notes

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