Tetrahydrofuran → HCID 57749306, compound

HRID 1874495Notes

Reaction equation

HRID 1874495 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]([CH2:10][C:11]([F:14])([F:13])[F:12])[N:3]=1.O1CCCC1.S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:26]=[C:27]([CH:44]=[CH:45][C:46]=1[CH3:47])[O:28][C:29]1[CH:30]=[CH:31][C:32]2[N:33]([N:35]=[C:36]([NH:38][C:39]([CH:41]3[CH2:43][CH2:42]3)=[O:40])[N:37]=2)[CH:34]=1>CN(C)C=O.CN(C)C(=O)C>[CH:41]1([C:39]([NH:38][C:36]2[N:37]=[C:32]3[CH:31]=[CH:30][C:29]([O:28][C:27]4[CH:44]=[CH:45][C:46]([CH3:47])=[C:25]([NH:24][C:7]([C:5]5[N:4]([CH2:10][C:11]([F:14])([F:13])[F:12])[N:3]=[C:2]([CH3:1])[CH:6]=5)=[O:9])[CH:26]=4)=[CH:34][N:33]3[N:35]=2)=[O:40])[CH2:42][CH2:43]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 133384343-Methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carboxylic acidHCID 57749401N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749306HCID 57749306, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 55 and using 3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carboxylic acid (82.8 mg, 0.398=mol), tetrahydrofuran (5 mL), thionyl chloride (69.1 μL, 0.796 mmol), N,N-dimethylformamide (2 drops), N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (117 mg, 0.362 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (151 mg, 81%) was obtained as a white solid.

Sources & evidence

ORD record
ord-f2d4e743b2f043fdac9da983a17cf7bd
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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