(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol → (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyl-[1,2,4]triazolo[4,3-a]quinolin-7-yl)acetic acid
Reaction equation
C(OC[C@@H](OC(C)(C)C)C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(N1CCOCC1)C=C2)(=[O:6])C(C)(C)C.[C:39]([O:43][C@@H:44]([C:47]1[C:48]([C:61]2[CH:66]=[CH:65][C:64]([Cl:67])=[CH:63][CH:62]=2)=[C:49]2[C:54](=[CH:55][C:56]=1[CH3:57])[N:53]1[CH:58]=[N:59][N:60]=[C:52]1[CH:51]=[CH:50]2)[CH2:45][OH:46])([CH3:42])([CH3:41])[CH3:40].C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(N1CCOCC1)C=C2)CO)(C)(C)C>>[C:39]([O:43][C@@H:44]([C:47]1[C:48]([C:61]2[CH:66]=[CH:65][C:64]([Cl:67])=[CH:63][CH:62]=2)=[C:49]2[C:54](=[CH:55][C:56]=1[CH3:57])[N:53]1[CH:58]=[N:59][N:60]=[C:52]1[CH:51]=[CH:50]2)[C:45]([OH:6])=[O:46])([CH3:42])([CH3:40])[CH3:41]Participants
4
Reactant 3
Product 1
Procedure
(S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyl-[1,2,4]triazolo[4,3-a]quinolin-7-yl)acetic acid was prepared in a similar manner as compound ((S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)acetic acid of Example 29 except using (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyl-[1,2,4]triazolo[4,3-a]quinolin-7-yl)ethanol instead of ((S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol. 1H-NMR 400 MHz (CD3OD) δ 9.95 (s, 1 H), 8.34 (s, 1 H), 7.6 (m, 3 H), 7.54 (m, 1 H), 7.35 (m, 2 H), 5.17 (s, 1 H), 2.75 (s, 3 H), 0.99 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C23H23ClN3O3: 424.1. Found: 424.2; LCMS-EST (m/z): [M−H]− calcd for C23H21ClN3O3: 422.1Found: 421.9.
Sources & evidence
- ORD record
- ord-1124e5e12c4f430aab0130ae86e88e03
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296758B2
Reaction notes
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