(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethanol → (2S)-2-tert-butoxy-2-(5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2,7-dimethylquinolin-6-yl)ethanol

HRID 931734Notes

Reaction equation

HRID 931734 reaction equation
C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1Cl)N=C(C)C=C2)CO)(C)(C)C.C([O:34][CH2:35][C@@H:36]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])[C:37]1[C:38]([C:49]2[C:58]3[C:53]4=[C:54]([CH2:59][CH2:60][O:61][C:52]4=[CH:51][CH:50]=2)[CH:55]=[CH:56][N:57]=3)=[C:39]2[C:44](=[CH:45][C:46]=1[CH3:47])[N:43]=[C:42]([CH3:48])[CH:41]=[CH:40]2)(=O)C(C)(C)C>>[C:63]([O:62][C@@H:36]([C:37]1[C:38]([C:49]2[C:58]3[C:53]4=[C:54]([CH2:59][CH2:60][O:61][C:52]4=[CH:51][CH:50]=2)[CH:55]=[CH:56][N:57]=3)=[C:39]2[C:44](=[CH:45][C:46]=1[CH3:47])[N:43]=[C:42]([CH3:48])[CH:41]=[CH:40]2)[CH2:35][OH:34])([CH3:66])([CH3:64])[CH3:65]

Participants

3

Reactant 2

HCID 66631657(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethanolHCID 66631664(2S)-2-tert-butoxy-2-(5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2,7-dimethylquinolin-6-yl)ethyl pivalate

Product 1

HCID 66632100(2S)-2-tert-butoxy-2-(5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2,7-dimethylquinolin-6-yl)ethanol

Procedure

Compound 6C was prepared following the procedure used to prepare compound 1K of Example 1 except that (2S)-2-tert-butoxy-2-(5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2,7-dimethylquinolin-6-yl)ethyl pivalate (6B) was used instead of compound 1J. LCMS-ESI+ (m/z): 433.3 (M+H)+.

Sources & evidence

ORD record
ord-cd67968ddc6442cab657f59094dad9bd
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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