1-Methylpiperazine → 4-methyl-N-[6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]piperazine-1-carboxamide

HRID 1664008Notes

Reaction equation

HRID 1664008 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:31]=[CH:32][CH:33]=1)[O:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20]([NH:22][C:23](=[O:30])OCC(Cl)(Cl)Cl)[N:21]=2)[N:18]=1)=[O:7].[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C(N(C(C)C)C(C)C)(C)C>CS(C)=O>[CH3:39][N:40]1[CH2:45][CH2:44][N:43]([C:23]([NH:22][C:20]2[N:21]=[C:16]3[CH:15]=[CH:14][C:13]([O:12][C:11]4[CH:31]=[CH:32][CH:33]=[C:9]([NH:8][C:6](=[O:7])[C:5]5[CH:34]=[CH:35][CH:36]=[C:3]([C:2]([F:38])([F:37])[F:1])[CH:4]=5)[CH:10]=4)=[N:18][N:17]3[CH:19]=2)=[O:30])[CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 61924TriisopropylamineHCID 575057352,2,2-Trichloroethyl[6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate

Product 1

HCID 575057374-methyl-N-[6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]piperazine-1-carboxamideYield 50.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using 2,2,2-trichloroethyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate (140 mg, 0.237 mmol), 1-methylpiperazine (40 μL, 0.356 mmol), N,N-diisopropylpropan-2-amine (123 μL, 0.713 mmol) and dimethyl sulfoxide (10 mL) as starting materials and in the same manner as in Example 386, the title compound (65 mg, 50%) was obtained as a pale-yellow powder.

Sources & evidence

ORD record
ord-7e3ea4f49e554c678862dfee7959ff61
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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