Diglycolamine → N-(3-{[2-({[2-(2-hydroxyethoxy)ethyl]carbamoyl}amino)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-3-(trifluoromethyl)benzamide

HRID 1664012Notes

Reaction equation

HRID 1664012 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].[NH2:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][OH:45].C(N(C(C)C)C(C)C)(C)C>CS(C)=O>[OH:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][NH:39][C:23]([NH:22][C:20]1[N:21]=[C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]3[CH:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:34]=[CH:35][CH:36]=[C:3]([C:2]([F:37])([F:1])[F:38])[CH:4]=4)[CH:33]=[CH:32][CH:31]=3)=[N:18][N:17]2[CH:19]=1)=[O:30]

Participants

5

Reactant 3

HCID 13578DiglycolamineHCID 61924TriisopropylamineHCID 575057352,2,2-Trichloroethyl[6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate

Product 1

HCID 57505740N-(3-{[2-({[2-(2-hydroxyethoxy)ethyl]carbamoyl}amino)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-3-(trifluoromethyl)benzamideYield 66.6%

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), 2-(2-aminoethoxy)ethanol (43 μL, 0.435 mmol), N,N-diisopropylpropane-2-amine (76 μL, 0.435 mmol) and dimethyl sulfoxide (5 mL) as starting materials and in the same manner as in Example 386, the title compound (86 mg, 62%) was obtained as a pale-yellow powder.

Sources & evidence

ORD record
ord-1d17b1ed6b714e9390d955eac899eeba
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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