(S)-1-Ethyl-2-methyl-piperazine → HCID 178462757, compound

HRID 579125Notes

Reaction equation

HRID 579125 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](O)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2].[CH2:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][C@@H:28]1[CH3:33])[CH3:26]>>[CH2:25]([N:27]1[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])=[CH:4][C:5]=4[CH3:24])[CH:10]=[N:11]3)=[N:16][CH:17]=2)=[O:20])[CH2:29][C@@H:28]1[CH3:33])[CH3:26]

Participants

3

Reactant 2

HCID 30634309(S)-1-Ethyl-2-methyl-piperazineHCID 178426451HCID 178426451, compound

Product 1

HCID 178462757HCID 178462757, compound

Procedure

The title compound was prepared in a manner similar to Example 112 using 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and (S)-1-ethyl-2-methylpiperazine. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.87-1.19 (m, 6 H) 2.42 (s, 3 H) 2.47 (br. s., 1 H) 2.52-2.59 (m, 1 H) 2.62-2.76 (m, 1 H) 2.77-2.98 (m, 2 H) 3.06 (d, J=10.61 Hz, 1 H) 3.35 (br. s., 1 H) 3.46-3.75 (m, 1 H) 4.05 (br. s., 1 H) 7.60 (dd, J=7.96, 1.64 Hz, 1 H) 7.66 (d, J=1.26 Hz, 1 H) 7.90 (d, J=8.34 Hz, 1 H) 8.01 (dd, J=8.72, 2.15 Hz, 1H) 8.06 (s, 1 H) 8.43 (d, J=8.59 Hz, 1 H) 8.51 (d, J=1.77 Hz, 1 H) 11.83-12.92 (m, 1 H); ESI-MS m/z [M+H]+ 431.3.

Sources & evidence

ORD record
ord-364f4d9f7c6e4a48857ca2698f2a0eb8
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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