(S)-1-(2-methyl-6-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-5-propoxy-3,4-dihydroquinolin-1(2H)-yl)ethanone → (S)-1-(5-cyclobutoxy-7,8-difluoro-2-methyl-6-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 1051606Notes

Reaction equation

HRID 1051606 reaction equation
Br[C:2]1[C:3]([O:18][CH:19]2[CH2:22][CH2:21][CH2:20]2)=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[F:12])[N:8]([C:14](=[O:16])[CH3:15])[C@@H:7]([CH3:17])[CH2:6][CH2:5]2.C[C@H]1CCC2C(=CC=C([C:38]3[CH:39]=[N:40][N:41]([CH:43]4[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]4)[CH:42]=3)C=2OCCC)N1C(=O)C>>[CH:19]1([O:18][C:3]2[C:2]([C:38]3[CH:39]=[N:40][N:41]([CH:43]4[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]4)[CH:42]=3)=[C:11]([F:12])[C:10]([F:13])=[C:9]3[C:4]=2[CH2:5][CH2:6][C@H:7]([CH3:17])[N:8]3[C:14](=[O:16])[CH3:15])[CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 118075413(S)-1-(2-methyl-6-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-5-propoxy-3,4-dihydroquinolin-1(2H)-yl)ethanoneHCID 118086274(S)-1-(6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

Product 1

HCID 118076358(S)-1-(5-cyclobutoxy-7,8-difluoro-2-methyl-6-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone

Procedure

(S)-1-(5-cyclobutoxy-7,8-difluoro-2-methyl-6-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)ethanone was synthesized from (S)-1-(6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone according to the procedures described above in Steps 2 and 3 of the synthesis of (S)-1-(2-methyl-6-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)-5-propoxy-3,4-dihydroquinolin-1(2H)-yl)ethanone (Example 4-1). 1H NMR (300 MHz, CD3OD) δ ppm 1.12-1.28 (m, 4H), 1.30-1.41 (m, 1H), 1.56-1.68 (m, 1H), 1.98-2.20 (m, 11H), 2.32-2.49 (m, 2H), 2.75-2.88 (m, 2H), 2.99-3.10 (m, 1H), 3.21-3.25 (m, 2H), 4.17-4.20 (m, 1H), 4.35-4.45 (m, 1H), 4.75-4.82 (m, 1H), 7.91 (s, 1H), 8.12 (s, 1H). MS (ESI, pos. ion) m/z 445 [M+H]+.

Sources & evidence

ORD record
ord-d8575d402f924c51a3ae90efa25a35f7
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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