(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-(4-chlorophenyl)-2-(dimethylcarbamoyl)-7-methylquinolin-6-yl)acetic acid

HRID 931771Notes

Reaction equation

HRID 931771 reaction equation
C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(CN(C)C1C=CC=CC=1)C=C2)C(O)=O)(C)(C)C.[C:37]([O:41][C@@H:42]([C:48]1[C:49]([C:64]2[CH:69]=[CH:68][C:67]([Cl:70])=[CH:66][CH:65]=2)=[C:50]2[C:55](=[CH:56][C:57]=1[CH3:58])[N:54]=[C:53]([C:59](=[O:63])[N:60]([CH3:62])[CH3:61])[CH:52]=[CH:51]2)[C:43]([O:45]CC)=[O:44])([CH3:40])([CH3:39])[CH3:38]>>[C:37]([O:41][C@@H:42]([C:48]1[C:49]([C:64]2[CH:65]=[CH:66][C:67]([Cl:70])=[CH:68][CH:69]=2)=[C:50]2[C:55](=[CH:56][C:57]=1[CH3:58])[N:54]=[C:53]([C:59](=[O:63])[N:60]([CH3:62])[CH3:61])[CH:52]=[CH:51]2)[C:43]([OH:45])=[O:44])([CH3:40])([CH3:38])[CH3:39]

Participants

3

Reactant 2

HCID 56644638(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino) methyl)quinolin-6-yl)acetic acidHCID 68595355(S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(dimethylcarbamoyl)-7-methylquinolin-6-yl)acetate

Product 1

HCID 56644856(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-(dimethylcarbamoyl)-7-methylquinolin-6-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-(dimethylcarbamoyl)-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-(4-chlorophenyl)-2-(dimethylcarbamoyl)-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) δ 7.91 (s, 1H), 7.87 (d, 1H), 7.65-7.58 (m, 3H), 7.50 (d, 1H), 7.40-7.32 (m, 1H), 5.23 (s, 1H), 3.18 (s, 3H), 3.05 (s, 3H), 2.69 (s, 3H), 0.99 (s, 9H); LCMS-ESI+ (m/z): [M+H]+ calcd for C25H28ClN2O4: 455.9. Found: 455.2, 457.2.

Sources & evidence

ORD record
ord-e6bfca1989574461995e374e7c0fcbe1
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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