N,N-Diethylaniline → HCID 58234999, compound

HRID 1187226Notes

Reaction equation

HRID 1187226 reaction equation
Br[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].C(N(CC)C1C=CC=CC=1)C.[C:37]([C:39]1[CH:40]=[C:41]([CH:44]=[C:45]([F:47])[CH:46]=1)[NH:42][CH3:43])#[CH:38]>CN(C=O)C>[C:37]([C:39]1[CH:40]=[C:41]([N:42]([CH3:43])[CH:2]([C:4]2[CH:5]=[C:6]([C:21]([N:23]([CH3:25])[CH3:24])=[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:44]=[C:45]([F:47])[CH:46]=1)#[CH:38]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 582349878-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamideHCID 86652723HCID 86652723, compound

Product 1

HCID 58234999HCID 58234999, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (185 mg, 0.37 mmol), N,N-diethylaniline (174 μl,1.10 mmol) and 3-ethynyl-5-fluoro-N-methylaniline (60 mg, 0.40 mmol) in DMF (1043 μl) were stirred at 50° C. for 2 days. Purification was done using an analogous procedure to the one described in Example 3.03 to give 8-(1-((3-ethynyl-5-fluorophenyl)(methyl)amino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (60 mg, 34%) as a white solid. Mass Spectrum: M+H+ 478. NMR Spectrum (DMSOd6): 1.55 (d, 3H), 2.62 (s, 3H), 2.92 (bs, 3H), 3.01 (bs, 3H), 3.18-3.27 (m, 2H), 3.28-3.33 (m partially hidden by H2O, 2H), 3.40-3.48 (m, 2H), 3.48-3.57 (m, 2H), 4.21 (s, 1H), 5.54 (q, 1H), 5.62 (s, 1H), 6.52 (d, 1H), 6.73 (d, 1H), 6.80 (s, 1H), 7.72 (d, 1H), 7.89 (d, 1H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-ef86af98960a4fcca06fda5fbac3ea6e
Source dataset
uspto-grants-2014_03
Patent number
US08673906B2

Reaction notes

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