N-Methylaniline → (S)-Ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(methyl(phenyl)carbamoyl) quinolin-6-yl)acetate

HRID 931772Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([CH3:34])=[C:11]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:7]=1)(=O)C.[CH3:35][NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:30]([O:29][C@@H:23]([C:11]1[C:12]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[C:13]2[C:8](=[CH:9][C:10]=1[CH3:34])[N:7]=[C:6]([C:5](=[O:4])[N:36]([CH3:35])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:15]=[CH:14]2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:31])([CH3:33])[CH3:32]

Participants

Reactant 2

HCID 7515N-Methylaniline

HCID 86691980(S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate

Product 1

HCID 68093221(S)-Ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(methyl(phenyl)carbamoyl) quinolin-6-yl)acetate

Procedure

(S)-Ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(methyl(phenyl)carbamoyl) quinolin-6-yl)acetate was prepared following the procedure used to prepare compound (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(dimethylcarbamoyl)-7-methylquinolin-6-yl)acetate of Example 16, except that N-methylaniline was used instead of dimethylamine HCl salt. LCMS-ESI+ (m/z): 545.2, 547.2 (M+H)+.

Sources & evidence

ORD record: ord-0010ba109cfa4012939ffed88cd50fae
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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