Methylamine → Methyl-{2-[4-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-pyrazol-1-yl]-ethyl}-amine

HRID 69258Notes

Reaction equation

HRID 69258 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([CH2:22][C:23]5[CH:24]=[C:25]6[C:30](=[CH:31][CH:32]=5)[N:29]=[CH:28][CH:27]=[CH:26]6)=[CH:20][N:21]=4)[N:18]=3)[CH:10]=[N:9]2)CCC[CH2:2]1.CN>CO>[CH3:2][NH:1][CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)=[CH:20][N:21]=3)[N:18]=2)[CH:10]=[N:9]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 579173086-{6-[1-(2-Pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-imidazo[1,2-b]pyridazin-3-ylmethyl}-quinoline

Product 1

HCID 57917321Methyl-{2-[4-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-pyrazol-1-yl]-ethyl}-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared in analogy to the compound of Example 236 using a 2 M solution of methylamine in MeOH instead of pyrrolidine (tR 2.61 min (conditions 3), MH+=384.3, 1H-NMR in DMSO-d6: 8.82 (m, 1H); 8.56 (s, 1H); 8.32 (m, 1H); 8.19 (s, 2H); 8.11 (d, 1H); 7.94 (m, 2H); 7.78 (m, 1H); 7.66 (s, 1H); 7.54 (d, 1H); 7.48 (dd, 1H); 4.53 (m, 4H); 3.40 (t, 2H); 2.55 (s, 3H)).

Sources & evidence

ORD record
ord-d4c226302c07451ba5b5d81cddd385f4
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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