(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol → (S)-2-tert-butoxy-2-(6-(4-chlorophenyl)-8-methyltetrazolo[1,5-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[N: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[N: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-methyltetrazolo[1,5-a]quinolin-7-yl)acetic acid (4.9 mg) 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-methyltetrazolo[1,5-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) 8.61 (s, 1 H), 7.75 (d, J=9.6 Hz, 1 H), 7.67-7.55 (m, 4 H), 7.39 (d, J=9.2 HZ, 1 H), 5.2 (s, 1 H), 2.79 (s, 3 H), 1.00 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C22H22ClN4O3: 425.1. Found: 425.1.
Sources & evidence
- ORD record
- ord-31d081c36293440c9f2adf0fefdde3e2
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296758B2
Reaction notes
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