(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino) methyl)quinolin-6-yl)acetic acid → (S)-2-tert-Butoxy-2-(5-cyclohexenyl-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acid
Reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:30]2[CH:35]=[CH:34][C:33](Cl)=[CH:32][CH:31]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][N:22]([CH3:29])[C:23]1C=CC=CC=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(O[C@@H](C1C(C2CCCCC=2)=C2C(=CC=1C)N=C(CN(C)C)C=C2)C(OCC)=O)(C)(C)C>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][N:22]([CH3:29])[CH3:23])[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 2
Product 1
Procedure
(S)-2-tert-Butoxy-2-(5-cyclohexenyl-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acid was prepared following the procedure used to prepare compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino) methyl)quinolin-6-yl)acetic acid of Example 14, except that (S)-ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-((dimethylamino) methyl)-7-methylquinolin-6-yl)acetate was used instead of (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino)methyl)quinolin-6-yl)acetate. 1H-NMR 300 MHz, (CD3OD) 8.40-8.30 (m, 1H), 7.85-7.78 (m, 1H), 7.42 (d, 1H), 6.04, 5.70 (br, br, 1H), 5.80, 5.64 (s, s, 1H), 4.65 (s, 2H), 3.04 (s, 6H), 2.68-2.56 (m, 4H), 2.40-1.80 (m, 6H), 1.30-1.20 (m, 9H); LCMS-ESI+ (m/z): [M-1-11]+ calcd for C25H34N2O3: 411.6. Found: 411.3.
Sources & evidence
- ORD record
- ord-82bed8e6d1614759a2bf9642c4c774c5
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296758B2
Reaction notes
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