(S)-N,N-Dimethylpiperidin-3-amine → HCID 178422201, compound

HRID 579094Notes

Reaction equation

HRID 579094 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[C:4]=1[F:25])#[N:2].[CH3:26][N:27]([CH3:34])[C@H:28]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]1>>[CH3:26][N:27]([CH3:34])[C@H:28]1[CH2:33][CH2:32][CH2:31][N:30]([C:19]([C:18]2[CH:22]=[CH:23][C:15]([N:12]3[C:13]([OH:14])=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:25])[C:5]=4[CH3:24])[CH:10]=[N:11]3)=[N:16][CH:17]=2)=[O:21])[CH2:29]1

Participants

3

Reactant 2

HCID 7330588(S)-N,N-Dimethylpiperidin-3-amineHCID 178422218HCID 178422218, compound

Product 1

HCID 178422201HCID 178422201, compound

Procedure

The title compound was prepared in a manner similar to Example 301 using 6-(4-(4-cyano-3-fluoro-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and (S)—N,N-dimethylpiperidin-3-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (d, J=11.12 Hz, 1 H) 1.78 (m, J=16.20 Hz, 2 H) 2.12 (d, J=10.86 Hz, 1 H) 2.33 (d, J=2.27 Hz, 3 H) 2.67-2.94 (m, 6 H) 3.13-4.79 (m, 5 H) 7.48-7.70 (m, 1 H) 7.70-7.80 (m, 1 H) 7.98-8.34 (m, 2 H) 8.57 (m, J=1.50 Hz, 2 H) 9.44-10.31 (m, 1 H). ESI-MS m/z [M+H]+ 449.3.

Sources & evidence

ORD record
ord-14cf5586c94946638b3e5a92e3ab699b
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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