HCID 20251947, compound → HCID 86728184, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]([NH2:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:14]([N:16]1[C:20](=[O:21])[C:19]([O:22]C)=[C:18]([C:24](O)=[O:25])[CH2:17]1)[CH3:15]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]([NH:13][C:24]([C:18]2[CH2:17][N:16]([CH2:14][CH3:15])[C:20](=[O:21])[C:19]=2[OH:22])=[O:25])[CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Procedure
By appropriate application of method described in Example 180, 4-(3,4-dichlorophenyl)butan-2-amine (racemic) (50 mg, 0.23 mmol) and 1-ethyl-4-methoxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (85 mg, 0.46 mmol) were converted to Example 225 (racemate) (12 mg, 0.032 mmol, 15% yield for two steps). HPLC/MS (Method D) RT=0.97 min, [M+1]+ 371.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.16-1.39 (m, 6H) 1.74-1.95 (m, 2H) 2.67 (t, J=7.78 Hz, 2H) 3.62 (q, J=7.03 Hz, 2H) 4.12 (s, 1H) 4.14-4.28 (m, 1H) 6.98-7.10 (m, 1H) 7.30 (d, J=1.25 Hz, 1H) 7.34 (d, J=8.28 Hz, 1H).
Sources & evidence
- ORD record
- ord-6ca05f172fab4733858e3edbf4c83e9f
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249096B2
Reaction notes
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