2,3,6-Trifluoroaniline → N,N-dimethyl-2-morpholino-4-oxo-8-(1-(2,3,6-trifluorophenylamino)ethyl)-4H-chromene-6-carboxamide

HRID 1947326Notes

Reaction equation

HRID 1947326 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].Br.Br[CH:13]([C:15]1[CH:16]=[C:17]([C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH:18]=[C:19]2[C:24]=1[O:23][C:22]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[CH:21][C:20]2=[O:31])[CH3:14]>>[CH3:36][N:34]([CH3:35])[C:32]([C:17]1[CH:18]=[C:19]2[C:24](=[C:15]([CH:13]([NH:4][C:3]3[C:5]([F:10])=[CH:6][CH:7]=[C:8]([F:9])[C:2]=3[F:1])[CH3:14])[CH:16]=1)[O:23][C:22]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[CH:21][C:20]2=[O:31])=[O:33]

Participants

3

Reactant 2

HCID 5222832,3,6-TrifluoroanilineHCID 671036758-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide

Product 1

HCID 58235093N,N-dimethyl-2-morpholino-4-oxo-8-(1-(2,3,6-trifluorophenylamino)ethyl)-4H-chromene-6-carboxamideYield 44.2%

Procedure

2,3,6-trifluoroaniline (0.086 mL, 0.82 mmol) was reacted with 8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (100 mg, 0.20 mmol) using an analogous procedure to the one described in Example 3.03 to give N,N-dimethyl-2-morpholino-4-oxo-8-(1-(2,3,6-trifluorophenylamino)ethyl)-4H-chromene-6-carboxamide (42 mg, 43%) as a white solid. Mass Spectrum: M+H+ 476. NMR Spectrum (DMSOd6): 1.56 (d, 3H), 2.75 (bs, 3H), 2.97 (bs, 3H), 3.50-3.59 (m, 4H), 3.69-3.80 (m, 4H), 5.38-5.47 (m, 1H), 5.57 (s, 1H), 6.05 (d, 1H), 6.60-6.70 (m, 1H), 6.86-6.96 (m, 1H), 7.73 (d, 1H), 7.76 (d, 1H).

Sources & evidence

ORD record
ord-17e505cfab8a4a1691e8614f25a193e8
Source dataset
uspto-grants-2013_03
Patent number
US08399460B2

Reaction notes

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