4-Fluoro-N-methylaniline → HCID 58235087, compound
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.Br.Br[CH:12]([C:14]1[CH:15]=[C:16]([C:31]([N:33]([CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])[CH3:34])=[O:32])[CH:17]=[C:18]2[C:23]=1[O:22][C:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[CH:20][C:19]2=[O:30])[CH3:13]>>[CH3:38][N:37]([CH3:39])[CH2:36][CH2:35][N:33]([CH3:34])[C:31]([C:16]1[CH:17]=[C:18]2[C:23](=[C:14]([CH:12]([N:6]([C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)[CH3:7])[CH3:13])[CH:15]=1)[O:22][C:21]([N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1)=[CH:20][C:19]2=[O:30])=[O:32]Participants
3
Procedure
4-fluoro-N-methylaniline (82 mg, 0.66 mmol) was reacted with 8-(1-bromoethyl)-N-(2-(dimethylamino)ethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (90 mg, 0.16 mmol) using a procedure similar to the one described in example 3.00 to give N-(2-(dimethylamino)ethyl)-8-(1-((4-fluorophenyl)(methyl)amino)ethyl)-N-methyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (39.0 mg, 46.4%) as a white solid. Mass Spectrum: M+H+ 511. NMR Spectrum: (DMSOd6) at 323° K: 1.55 (d, 3H), 2.04 (bs, 6H), 2.40 (bs, 2H), 2.68 (s, 3H), 2.93 (s, 3H), 3.22-3.36 (m, 4H), 3.37 (bs, 2H), 3.44-3.58 (m, 4H), 5.45 (q, 1H), 5.50 (s, 1H), 6.82 (dd, 2H), 7.01 (dd, 2H), 7.56 (d, 1H), 7.83 (d, 1H).
Sources & evidence
- ORD record
- ord-5be55b48967340f49dc9fd8f8a2ee906
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673906B2
Reaction notes
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