Tetrahydrofuran → HCID 57505648, compound

HRID 1668099Notes

Reaction equation

HRID 1668099 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([OH:8])=O)(=[O:4])=[O:3].O1CCCC1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:21][C:22]1[N:23]=[C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([CH3:47])=[C:35]([NH:37][C:38]([C:40]4[N:44]([CH3:45])[N:43]=[C:42]([CH3:46])[CH:41]=4)=[O:39])[CH:36]=3)=[N:26][N:25]2[CH:48]=1>CN(C)C=O.CN(C)C(=O)C>[CH3:45][N:44]1[C:40]([C:38]([NH:37][C:35]2[CH:36]=[C:31]([O:30][C:27]3[CH:28]=[CH:29][C:24]4[N:25]([CH:48]=[C:22]([NH:21][C:6](=[O:8])[CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[N:23]=4)[N:26]=3)[CH:32]=[CH:33][C:34]=2[CH3:47])=[O:39])=[CH:41][C:42]([CH3:46])=[N:43]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 37328412-Methanesulfonylacetic acidHCID 57505635N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride

Product 1

HCID 57505648HCID 57505648, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 279 and using (methylsulfonyl)acetic acid (100 mg, 0.73 mmol), tetrahydrofuran (1.5 mL), N,N-dimethylformamide (1 drop), oxalyl chloride (63 μL, 0.73 mmol), N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride (200 mg, 0.48 mmol) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (91 mg, 38%) was obtained as a pale-yellow solid.

Sources & evidence

ORD record
ord-9392514b078c45b9b4173c75f6343e12
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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