6-{[6-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]methyl}quinoline → 6-[6-(1-Piperidin-4-yl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline

HRID 69162Notes

Reaction equation

HRID 69162 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][CH:21]=[CH:20]5)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1.CC1(C)C(C)OB([C:34]2C=N[N:37]([CH:39]3CCN(C(OC(C)(C)C)=O)C[CH2:40]3)[CH:38]=2)O1>>[NH:37]1[CH2:39][CH2:40][CH:1]([N:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]4[N:11]([C:13]([CH2:16][C:17]5[CH:18]=[C:19]6[C:24](=[CH:25][CH:26]=5)[N:23]=[CH:22][CH:21]=[CH:20]6)=[CH:14][N:15]=4)[N:12]=3)[CH:4]=[N:3]2)[CH2:34][CH2:38]1

Participants

3

Reactant 2

HCID 442060636-{[6-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]methyl}quinolineHCID 68631873Tert-butyl 4-(4-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 442060686-[6-(1-Piperidin-4-yl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-quinoline

Procedure

The title compound was prepared in analogy to the synthesis of compound of Example 2, using tert-butyl 4-(4-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate and with an additional deprotection step before final reduction (tR 1.0 min (conditions 1), MH+=410).

Sources & evidence

ORD record
ord-8a01ab6c807f4f01bebe3e6ab26d33d5
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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