Tetrahydrofuran → HCID 57749086, compound

HRID 1874506Notes

Reaction equation

HRID 1874506 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](O)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.O1CCCC1.S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:25]=[C:26]([CH:43]=[CH:44][C:45]=1[Cl:46])[O:27][C:28]1[CH:29]=[CH:30][C:31]2[N:32]([N:34]=[C:35]([NH:37][C:38]([CH:40]3[CH2:42][CH2:41]3)=[O:39])[N:36]=2)[CH:33]=1>CN(C)C=O.CN(C)C(=O)C>[Cl:46][C:45]1[CH:44]=[CH:43][C:26]([O:27][C:28]2[CH:29]=[CH:30][C:31]3[N:32]([N:34]=[C:35]([NH:37][C:38]([CH:40]4[CH2:42][CH2:41]4)=[O:39])[N:36]=3)[CH:33]=2)=[CH:25][C:24]=1[NH:23][C:7]([C:5]1[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:8]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 27756651-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 57749285N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749086HCID 57749086, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 55 and using 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (70.8 mg, 0.365 mmol), tetrahydrofuran (5 mL), thionyl chloride (63.3 μL, 0.730 mmol), N,N-dimethylformamide (2 drops), N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (112 mg, 0.326 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (63.6 mg, 38%) was obtained as a white solid.

Sources & evidence

ORD record
ord-d0d5c44b8af44d31b08942000c4aff26
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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