3-Bromo-5-fluorobenzonitrile → 8-(1-(3-cyano-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

HRID 572798Notes

Reaction equation

HRID 572798 reaction equation
[NH2:1][CH:2]([C:4]1[CH:5]=[C:6]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[CH:10][C:9]2=[O:20])[CH3:3].Br[C:27]1[CH:28]=[C:29]([CH:32]=[C:33]([F:35])[CH:34]=1)[C:30]#[N:31]>>[C:30]([C:29]1[CH:28]=[C:27]([NH:1][CH:2]([C:4]2[CH:5]=[C:6]([C:21]([N:23]([CH3:24])[CH3:25])=[O:22])[CH:7]=[C:8]3[C:13]=2[O:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][C:9]3=[O:20])[CH3:3])[CH:34]=[C:33]([F:35])[CH:32]=1)#[N:31]

Participants

3

Reactant 2

HCID 27833303-Bromo-5-fluorobenzonitrileHCID 582349768-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Product 1

HCID 582350128-(1-(3-cyano-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamideYield 82%

Procedure

8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (300 mg, 0.87 mmol, [α]D20°: +35° in acetonitrile) was reacted with 3-bromo-5-fluorobenzonitrile (382 mg, 1.91 mmol) using a procedure similar to the one described in Example 8.00. Purification was done by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM followed by preparative HPLC on a Waters X-Bridge system. The fractions containing the desired compound were evaporated to dryness to afford 8-(1-(3-cyano-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (330 mg, 82%) as a clear white solid. Mass Spectrum: M+H+ 465.

Workup

  1. customPurification
  2. additionThe fractions containing the desired compound
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-0edd6d2d65d743478d380035740434d1
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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