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

HRID 11327Notes

Reaction equation

HRID 11327 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:13](=O)[CH3:14].[CH3:16][C:17]1[N:18]=[C:19]([C:25]2S[CH:27]=[CH:28][CH:29]=2)S[C:21]=1[C:22](=O)[CH3:23].[NH3:30]>>[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:13][C:3]2[C:2](=[CH:27][CH:28]=[C:29]([CH2:25][CH2:19][N:18]3[CH2:23][CH2:22][CH2:21][C@H:17]3[CH3:16])[CH:4]=2)[N:30]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27442451-[4-Methyl-2-(2-thienyl)-1,3-thiazol-5-yl]-1-ethanoneHCID 28055541-[5-methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]ethan-1-one

Product 1

HCID 11603648(R)-2-(5-methyl-1-(pyridin-2-yl)-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-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-ethanone (Singh, S. P., et. al. Heterocycl. Commun., 2001, 7(1), p. 49-54) for 1-(4-methyl-2-thiophen-2-yl-thiazol-5-yl)-ethanone. 1H NMR (300 MHz, CDCl3) δ 1.14 (d, J=6.10 Hz, 3H), 1.46 (m, 1H), 1.77 (m, 2H), 1.96 (m, 1H), 2.25 (q, J=8.82 Hz, 1H), 2.40 (m, 2H), 3.01 (m, 2H), 3.06 (s, 3H), 3.13 (m, 1H), 3.30 (td, J=8.56, 2.54 Hz, 1H), 7.26 (m, 1H), 7.61 (m, 3H), 7.87 (m, 2H), 8.03 (d, J=8.48 Hz, 1H), 8.11 (d, J=8.82 Hz, 1H), 8.13 (s, 1H), 8.53 (m, 1H); MS (DCI-NH3) [M+H]+ at 398.

Sources & evidence

ORD record
ord-cf53b5edf2234da68927f86642b87876
Source dataset
uspto-grants-2006_08
Patent number
US07098222B2

Reaction notes

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