(5-Bromo-1,3-thiazol-2-yl)methanol → 4-(2,3-Dimethylphenoxy)-1-(5-(2-(hydroxymethyl)thiazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

HRID 2175234Notes

Reaction equation

HRID 2175234 reaction equation
[CH3:1][C:2]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15](C3C=CN=C(C(OC)=O)C=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].BrC1C=CN=C(C(OC)=O)C=1.Br[C:47]1[S:51][C:50]([CH2:52][OH:53])=[N:49][CH:48]=1>>[CH3:1][C:2]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:48]3[N:49]=[C:50]([CH2:52][OH:53])[S:51][CH:47]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

4

Reactant 3

HCID 11953783(5-Bromo-1,3-thiazol-2-yl)methanolHCID 12828947Methyl 4-bromopicolinateHCID 70982851Methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinate

Product 1

HCID 709819774-(2,3-Dimethylphenoxy)-1-(5-(2-(hydroxymethyl)thiazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

Procedure

The title compound was prepared using a procedure analogous to methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinate except that methyl 4-bromopicolinate was replaced with (5-bromothiazol-2-yl)methanol. LCMS, [M+H]+=437.1. 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J=7.0 Hz, 1H), 7.26-7.19 (m, 2H), 7.06 (s, 1H), 7.03-6.95 (m, 1H), 6.73 (d, J=7.5 Hz, 1H), 6.63 (d, J=8.2 Hz, 1H), 5.01 (s, 2H), 3.92 (t, J=5.2 Hz, 2H), 3.79 (t, J=6.9 Hz, 2H), 2.74 (t, J=7.3 Hz, 2H), 2.62 (t, J=6.2 Hz, 2H), 2.25-2.11 (m, 5H), 1.93 (s, 3H), 1.89-1.80 (m, 2H).

Sources & evidence

ORD record
ord-905507041f944932852f59bdec2cbeb1
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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