Morpholine → HCID 178523133, compound
Reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[O:19][C:18]([CH2:20][CH2:21][NH:22][C:23]([C:25]3[NH:29][N:28]=[C:27]([C:30](O)=[O:31])[CH:26]=3)=[O:24])=[CH:17][CH:16]=2)[CH:11]=[CH:12][C:13]=1[Cl:14]>>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[O:19][C:18]([CH2:20][CH2:21][NH:22][C:23]([C:25]3[NH:29][N:28]=[C:27]([C:30]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:31])[CH:26]=3)=[O:24])=[CH:17][CH:16]=2)[CH:11]=[CH:12][C:13]=1[Cl:14]Participants
3
Procedure
The title compound was prepared as in Example 1 starting from morpholine and 5-{2-[5-(3,4-dichlorophenyl)furan-2-yl]ethylcarbamoyl}-1H-pyrazole-3-carboxylic acid. Crude product was purified by chromatography (CombiFlash, 1st column silica, eluent: 0-10% MeOH/DCM: 2nd column C-18 RP, eluent: 0-100% MeCN/water) to give 505 mg (17%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.95 (t, 1H), 3.56 (q, 1H), 3.62 (br s, 6H), 3.90 (br s, 2H), 6.34 (d, 1H), 7.02 (d, 1H), 7.08 (s, 1H), 7.62 (m, 2H), 7.85 (d, 1H), 8.61 (s, 1H), 13.94 (s, 1H).
Workup
- customCrude product was purified by chromatography (CombiFlash, 1st column silica, eluent: 0-10% MeOH/DCM: 2nd column C-18 RP, eluent: 0-100% MeCN/water)
Sources & evidence
- ORD record
- ord-e6ea50c6f8794c78bd870250a91cf53e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975254B2
Reaction notes
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