HCID 56644430, compound → HCID 56644854, compound

HRID 931777Notes

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]([C:21]([O:23]C)=[O:22])[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(CN(C)C1C=CC=CC=1)C=C2)CO)(C)(C)C>>[C:1]([O:5][C@H:6]([C:7]([OH:9])=[O:8])[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]([C:21]([OH:23])=[O:22])[CH:14]=[CH:13]2)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 56644430HCID 56644430, compound

HCID 66631677HCID 66631677, compound

Product 1

HCID 56644854HCID 56644854, compound

Procedure

(S)-6-(tert-Butoxy(carboxy)methyl)-5-(4-chlorophenyl)-7-methylquinoline-2-carboxylic acid was prepared following the procedure used to prepare compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(methoxycarbonyl)-7-methylquinolin-6-yl)acetic acid of Example 12, except that (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino)methyl)quinolin-6-yl)ethanol was used instead of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(methoxymethyl)-7-methylquinolin-6-yl)ethanol. 1H-NMR 300 MHz, (CD3OD). δ8.15-8.05 (m, 2H), 7.93 (d, 1H), 7.70-7.60 (m, 3H), 7.40-7.35 (m, 1H), 5.24 (s, 1H), 2.70 (s, 3H), 0.99 (s, 9H); LCMS-ESI+ (m/z): [M+H]+ calcd for C23H23ClNO5: 428.9. Found: 428.1, 430.1.

Sources & evidence

ORD record: ord-b7e6d0e47bb54483aa579eaa0fc19a5e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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