1-Cyclobutylpiperazine → HCID 178426408, compound

HRID 579128Notes

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].[CH:25]1([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26]1>>[CH:25]1([N:29]2[CH2:34][CH2:33][N:32]([C:19]([C:18]3[CH:22]=[CH:23][C:15]([N:12]4[C:13]([OH:14])=[C:9]([C:6]5[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=5[CH3:24])[CH:10]=[N:11]4)=[N:16][CH:17]=3)=[O:20])[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26]1

Participants

Reactant 2

HCID 47386021-Cyclobutylpiperazine

HCID 178426451HCID 178426451, compound

Product 1

HCID 178426408HCID 178426408, 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 1-cyclobutylpiperazine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58-1.71 (m, 2 H) 1.76-1.90 (m, 2 H) 1.90-2.07 (m, 2 H) 2.37 (br. s., 4 H) 2.42 (s, 3 H) 2.83 (quin, J=7.71 Hz, 1 H) 3.44 (d, J=7.07 Hz, 2 H) 3.64 (br. s., 2 H) 7.63 (dd, J=7.96, 1.64 Hz, 1 H) 7.69 (s, 1 H) 7.84 (d, J=8.08 Hz, 1 H) 8.03 (dd, J=8.59, 2.27 Hz, 1 H) 8.11 (s, 1 H) 8.40 (d, J=8.59 Hz, 1 H) 8.52 (dd, J=2.27, 0.76 Hz, 1 H); ESI-MS m/z [M+H]+ 443.3.

Sources & evidence

ORD record: ord-43fdbe977dc845c1ba2d704c095fc5b4
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040522B2

Reaction notes

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