Dimethylformamide → HCID 57505602, compound

HRID 1668053Notes

Reaction equation

HRID 1668053 reaction equation
[C:1](O)(=O)[C:2]#[C:3]C.C[N:8]([CH3:11])[CH:9]=[O:10].C(Cl)(=O)C(Cl)=O.N[C:19]1[CH:20]=[C:21]([CH:38]=[CH:39][C:40]=1F)[O:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([CH:29]=[C:30]([NH:32][C:33]([CH:35]3[CH2:37][CH2:36]3)=[O:34])[N:31]=2)[N:28]=1>CN(C)C(=O)C.O1CCCC1>[C:9]([NH:8][C:11]1[CH:20]=[C:21]([CH:38]=[CH:39][C:40]=1[CH3:19])[O:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([CH:29]=[C:30]([NH:32][C:33]([CH:35]3[CH2:36][CH2:37]3)=[O:34])[N:31]=2)[N:28]=1)(=[O:10])[C:1]#[C:2][CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 685352-Butynoic acidHCID 57505446N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57505602HCID 57505602, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

Using 2-butynoic acid (78 mg, 0.93 mmol), tetrahydrofuran (4.0 mL), N,N-dimethylformamide (20 μL, 0.26 mmol), oxalyl chloride (81 μL, 0.93 mmol), N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.62 mmol) and N,N-dimethylacetamide (4.0 mL), and in the same manner as in Example 238, the title compound (47 mg, 20%) was obtained as a white powder.

Sources & evidence

ORD record
ord-f387093ea0b14bc487bceb7acb35f67e
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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