1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 51356769, compound
Reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][CH:11]1[NH:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:39]([C:41]1[C:57]([F:58])=[CH:56][C:44]([O:45][C:46]2[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][C:47]=2[F:55])=[C:43]([O:59]C)[CH:42]=1)[CH3:40]>ClCCl.O>[CH2:39]([C:41]1[C:57]([F:58])=[CH:56][C:44]([O:45][C:46]2[CH:54]=[CH:53][C:49]([C:50]([N:16]3[CH2:15][CH2:14][NH:13][C:12](=[O:17])[CH:11]3[CH3:10])=[O:51])=[CH:48][C:47]=2[F:55])=[C:43]([OH:59])[CH:42]=1)[CH3:40]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
N,N-Diisopropylethylamine (74 μL, 0.42 mmol), 3-methylpiperazin-2-one (23.3 mg, 0.20 mmol), EDCI (39.1 mg, 0.20 mmol) and HOBt (27.6 g, 0.20 mmol) were successively added to a suspension of 4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid (which may be prepared in accordance with the experimental described in Example 4, step 4; 50 mg, 0.17 mmol) in dichloromethane (0.55 mL). The reaction mixture was stirred at room temperature overnight then diluted by addition of dichloromethane (10 mL) and water (10 mL). After separation, the organic layer was washed with water (10 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (98:2 to 95:5) as eluent. The title product was obtained as a white solid (24 mg, 36%).
Workup
- custommay be prepared in accordance with the
- customAfter separation
- washthe organic layer was washed with water (10 mL)
- dry with materialThe organic phase was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-38d5c65b873240e484ceb314d129b9d6
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623865B2
Reaction notes
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