Tetrahydrofuran → HCID 57749393, compound

HRID 1874505Notes

Reaction equation

HRID 1874505 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=[N:3]1.O1CCCC1.S(Cl)(Cl)=O.[NH2:19][C:20]1[CH:21]=[C:22]([CH:39]=[CH:40][C:41]=1[Cl:42])[O:23][C:24]1[CH:25]=[CH:26][C:27]2[N:28]([N:30]=[C:31]([NH:33][C:34]([CH:36]3[CH2:38][CH2:37]3)=[O:35])[N:32]=2)[CH:29]=1>CN(C)C=O.CN(C)C(=O)C>[Cl:42][C:41]1[CH:40]=[CH:39][C:22]([O:23][C:24]2[CH:25]=[CH:26][C:27]3[N:28]([N:30]=[C:31]([NH:33][C:34]([CH:36]4[CH2:38][CH2:37]4)=[O:35])[N:32]=3)[CH:29]=2)=[CH:21][C:20]=1[NH:19][C:7]([C:6]1[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=1)=[O:9]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 6431581-methyl-1H-pyrazole-5-carboxylic acidHCID 57749285N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749393HCID 57749393, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 55 and using 1-methyl-1H-pyrazole-5-carboxylic acid (46.1 mg, 0.366 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 (114 mg, 0.332 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (69.5 mg, 46%) was obtained as a white solid.

Sources & evidence

ORD record
ord-085f49c43b974f76a95e7b68597d507b
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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