(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acid → (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methylamino)methyl)quinolin-6-yl)acetic acid

HRID 931758Notes

Reaction equation

HRID 931758 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][N:22](C)[CH3:23])[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(CNC)C=C2)CO)(C)(C)C>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([CH2:21][NH:22][CH3:23])[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 56644427(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acidHCID 66631556(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methylamino)methyl)quinolin-6-yl)ethanol

Product 1

HCID 56644428(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methylamino)methyl)quinolin-6-yl)acetic acid

Procedure

Following the procedure used to prepare compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acid (9) of Example 9, except that (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methylamino)methyl)quinolin-6-yl)ethanol was used instead of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethanol. 1H-NMR 300 MHz, (CD3OD) δ7.95 (s, 1H), 7.74 (d, 1H), 7.65-7.55 (m, 3H), 7.35-7.28 (m, 2H), 5.22 (s, 1H), 4.51 (s, 2H), 2.88 (s, 3H), 2.67 (s, 3H), 0.98 (s, 9H); LCMS-ESI+ (m/z): [M+H]+ calcd for C24H27ClN2O3: 427.9. Found: 427.2, 429.2.

Sources & evidence

ORD record
ord-f9429210519a49838cbfb28241a7a5f8
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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