4-Fluoroaniline → HCID 58235064, compound

HRID 572810Notes

Reaction equation

HRID 572810 reaction equation
Br[CH:2]([C:4]1[CH:5]=[C:6]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][C@@H:16]([CH3:20])[CH2:15]1)=[CH:10][C:9]2=[O:21])[CH3:3].[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1>CC(N(C)C)=O>[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][CH:2]([C:4]2[CH:5]=[C:6]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[CH:7]=[C:8]3[C:13]=2[O:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][C@@H:16]([CH3:20])[CH2:15]2)=[CH:10][C:9]3=[O:21])[CH3:3])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 58234991HCID 58234991, compound

Product 1

HCID 58235064HCID 58235064, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

8-(1-bromoethyl)-N,N-dimethyl-2-((S)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamide (110 mg, 0.20 mmol) and 4-fluoroaniline in DMA (1 mL) were stirred at 50° C. for 5 hrs. The reaction mixture was purified by preparative HPLC on a Waters X-Bridge system. The fractions containing the desired compound were concentrated. The obtained gum was triturated in diethyl ether and petroleum ether, the resulting solid was collected by filtration and dried to afford 8-(1-(4-fluorophenylamino)ethyl)-N,N-dimethyl-2-((S)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamide (45 mg, 51%) as a white solid. Mass Spectrum: M+H+ 545. NMR Spectrum (CDCl3): 1.25 (d, 1.5H), 1.26 (d, 1.5H), 1.61 (d, 3H), 2.77-2.88 (m, 1H), 2.83 (bs, 3H), 3.06 (bs, 3H), 3.13-3.22 (m, 1H), 3.64-3.82 (m, 4H), 3.97 (bs, 1H), 3.98-4.06 (m, 1H), 4.91 (q, 1H), 5.56 (s, 1H), 6.37-6.43 (m, 2H), 6.82 (t, 2H), 7.73 (d, 1H), 8.11 (d, 1H).

Workup

  1. customThe reaction mixture was purified by preparative HPLC on a Waters X-Bridge system
  2. additionThe fractions containing the desired compound
  3. concentrationwere concentrated
  4. customThe obtained gum was triturated in diethyl ether
  5. filtrationpetroleum ether, the resulting solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-461e2f073fa04125b914754b644f7eaf
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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