3-Amino-5-fluorobenzonitrile → 8-(1-(3-cyano-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].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]>>[C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH:13]([C:15]2[CH:16]=[C:17]([C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH:18]=[C:19]3[C:24]=2[O:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][C:20]3=[O:31])[CH3:14])[CH:9]=[C:8]([F:10])[CH:7]=1)#[N:6]Participants
3
Procedure
3-amino-5-fluorobenzonitrile (0.111 g, 0.82 mmol) was reacted with 8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (0.1 g, 0.20 mmol) using an analogous procedure to the one described in Example 3.03 to give 8-(1-(3-cyano-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (0.052 g, 55%) as a white solid. Mass Spectrum: M+H+ 465. NMR Spectrum (CDCl3): 1.62 (d, 3H), 2.92 (bs, 3H), 3.08 (bs, 3H), 3.45-3.58 (m, 4H), 3.82-3.91 (m, 4H), 4.61 (d, 1H), 4.88-4.97 (m, 1H), 5.57 (s, 1H), 6.36 (ddd, 1H), 6.49 (dd, 1H), 6.65 (ddd, 1H), 7.70 (d, 1H), 8.14 (d, 1H).
Sources & evidence
- ORD record
- ord-9a806866721043d084406f370ff35afe
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673906B2
Reaction notes
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