Ammonia → (R)-2-(5-chloro-1-methyl-3-phenyl-1H-pyrazol-4-yl)-6-(2-(2-methylpyrrolidin-1-yl)ethyl)quinoline

HRID 11334Notes

Reaction equation

HRID 11334 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14](=O)[CH3:15].[CH3:17][C:18]1[N:19]=[C:20]([C:26]2S[CH:28]=[CH:29][CH:30]=2)S[C:22]=1[C:23](=O)[CH3:24].[NH3:31]>>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14]1[CH:15]=[CH:14][C:3]2[C:2](=[CH:28][CH:29]=[C:30]([CH2:26][CH2:20][N:19]3[CH2:24][CH2:23][CH2:22][C@H:18]3[CH3:17])[CH:4]=2)[N:31]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27442451-[4-Methyl-2-(2-thienyl)-1,3-thiazol-5-yl]-1-ethanoneHCID 27635191-(5-chloro-1-methyl-3-phenyl-1H-pyrazol-4-yl)-1-ethanone

Product 1

HCID 11618861(R)-2-(5-chloro-1-methyl-3-phenyl-1H-pyrazol-4-yl)-6-(2-(2-methylpyrrolidin-1-yl)ethyl)quinoline

Procedure

The title compound was prepared using the procedure described in Example 1G using 1-(5-chloro-1-methyl-3-phenyl-1H-pyrazol-4-yl)-ethanone for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.15 (d, J=6.10 Hz, 3H), 1.48 (m, 1H), 1.78 (m, 2H), 1.96 (m, 1H), 2.27 (q, J=8.59 Hz, 1H), 2.41 (m, 2H), 3.03 (m, 2H), 3.15 (m, 1H), 3.31 (m, 1H), 3.99 (s, 3H), 7.26 (m, 4H), 7.46 (m, 2H), 7.62 (m, 2H), 8.00 (d, J=8.48 Hz, 1H), 8.05 (d, J=8.14 Hz, 1H); MS (DCI-NH3) [M+H]+ at 431.

Sources & evidence

ORD record
ord-b303602573e54ce8b33be763675c3f1a
Source dataset
uspto-grants-2006_08
Patent number
US07098222B2

Reaction notes

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