(R)-N,N-Dimethylpiperidin-3-amine → HCID 178422200, compound

HRID 526591Notes

Reaction equation

HRID 526591 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 7330586(R)-N,N-Dimethylpiperidin-3-amineHCID 178422218HCID 178422218, compound

Product 1

HCID 178422200HCID 178422200, 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 (R)—N,N-dimethylpiperidin-3-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.53 (d, J=13.18 Hz, 1H) 1.77 (m, J=16.10 Hz, 2H) 2.10 (br. s., 1H) 2.33 (s, 3H) 2.57-2.89 (m, 6H) 2.90-4.77 (m, 5H) 7.63 (br. s., 1H) 7.74 (t, J=7.54 Hz, 1H) 8.09 (d, J=7.81 Hz, 1H) 8.24 (br. s., 1H) 8.35-8.66 (m, 2H) 9.86 (br. s., 1H). ESI-MS m/z [M+H]+ 449.3.

Sources & evidence

ORD record
ord-ba4c3cf41e1d4649a72870f6d095f461
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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