PIPERIDINE, 1-(3-AZETIDINYL)-, DIHYDROCHLORIDE → HCID 178426405, compound

HRID 526614Notes

Reaction equation

HRID 526614 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])[CH:4]=1)#[N:2].Cl.Cl.[NH:27]1[CH2:30][CH:29]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:28]1>>[OH:14][C:13]1[N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([N:27]3[CH2:30][CH:29]([N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[CH2:28]3)=[O:21])=[CH:17][N:16]=2)[N:11]=[CH:10][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[CH3:24]

Participants

3

Reactant 2

HCID 23224633PIPERIDINE, 1-(3-AZETIDINYL)-, DIHYDROCHLORIDEHCID 178426451HCID 178426451, compound

Product 1

HCID 178426405HCID 178426405, 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-(azetidin-3-yl)piperidine dihydrochloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36 (d, J=4.80 Hz, 2H) 1.41-1.54 (m, 4H) 2.23-2.34 (m, 3H) 2.36 (s, 3H) 3.13-3.21 (m, 1H) 3.86 (dd, J=9.47, 4.67 Hz, 1H) 4.05 (t, J=8.46 Hz, 1H) 4.20 (d, J=4.80 Hz, 1H) 4.28-4.43 (m, 1H) 7.55 (dd, J=8.08, 1.52 Hz, 1H) 7.62 (s, 1H) 7.78 (d, J=8.08 Hz, 1H) 8.03 (s, 1H) 8.15 (dd, J=8.72, 2.40 Hz, 1H) 8.35 (d, J=8.84 Hz, 1H) 8.65 (dd, J=2.27, 0.76 Hz, 1H) 12.19-13.21 (m, 1H); ESI-MS m/z [M+H]+ 443.3

Sources & evidence

ORD record
ord-fd97b24f31a344e2a8b7ee37942b0f1a
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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