1-(Azetidin-3-yl)piperidinato → HCID 178422208, compound

HRID 526606Notes

Reaction equation

HRID 526606 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].[NH:26]1[CH2:29][CH:28]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:27]1>>[F:25][C:4]1[C:5]([CH3:24])=[C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([N:26]4[CH2:29][CH:28]([N:30]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]5)[CH2:27]4)=[O:21])=[CH:17][N:16]=3)[C:13]=2[OH:14])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

3

Reactant 2

HCID 193911521-(Azetidin-3-yl)piperidinatoHCID 178422218HCID 178422218, compound

Product 1

HCID 178422208HCID 178422208, compound

Procedure

The title compound was prepared in a manner similar to Example 303 using 6-(4-(4-cyano-3-fluoro-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid and 1-(azetidin-3-yl)piperidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22-2.00 (m, 6H) 2.33 (d, J=2.27 Hz, 3H) 2.84 (br. s., 2H) 3.23-3.70 (m, 2H) 4.06-4.19 (m, 1H) 4.33 (br. s., 2H) 4.61 (br. s., 1H) 4.66-4.77 (m, 1H) 7.63 (d, J=7.07 Hz, 1H) 7.75 (t, J=7.45 Hz, 1H) 7.98-8.89 (m, 4H). ESI-MS m/z [M+H]+ 461.3.

Sources & evidence

ORD record
ord-3a7e4dfcea934881a189ed1c87c0d71f
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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