Tetrahydrofuran → HCID 57505657, compound

HRID 1668110Notes

Reaction equation

HRID 1668110 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]([OH:6])=O.O1CCCC1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:19][C:20]1[N:21]=[C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([CH3:45])=[C:33]([NH:35][C:36]([C:38]4[N:42]([CH3:43])[N:41]=[C:40]([CH3:44])[CH:39]=4)=[O:37])[CH:34]=3)=[N:24][N:23]2[CH:46]=1>CN(C)C=O.CN(C)C(=O)C>[CH3:43][N:42]1[C:38]([C:36]([NH:35][C:33]2[CH:34]=[C:29]([O:28][C:25]3[CH:26]=[CH:27][C:22]4[N:23]([CH:46]=[C:20]([NH:19][C:4]([CH:2]5[CH2:3][O:1]5)=[O:6])[N:21]=4)[N:24]=3)[CH:30]=[CH:31][C:32]=2[CH3:45])=[O:37])=[CH:39][C:40]([CH3:44])=[N:41]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 94158Glycidic 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 57505657HCID 57505657, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 279 and using oxirane-2-carboxylic acid (54 mg, 0.62 mmol), tetrahydrofuran (1.5 mL), N,N-dimethylformamide (1 drop), oxalyl chloride (53 μL, 0.62 mmol), N-{5-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide hydrochloride (170 mg, 0.41 mmol) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (96 mg, 52%) was obtained as a white solid.

Sources & evidence

ORD record
ord-3ecfdfc59b4c4ebea82b0c23158eabe9
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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