Tetrahydrofuran → HCID 57749202, compound

HRID 1874488Notes

Reaction equation

HRID 1874488 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[N:3]1.O1CCCC1.S(Cl)(Cl)=O.[NH2:19][C:20]1[CH:21]=[C:22]([CH:39]=[CH:40][C:41]=1[CH3:42])[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>[CH:36]1([C:34]([NH:33][C:31]2[N:32]=[C:27]3[CH:26]=[CH:25][C:24]([O:23][C:22]4[CH:39]=[CH:40][C:41]([CH3:42])=[C:20]([NH:19][C:7]([C:4]5[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=5)=[O:9])[CH:21]=4)=[CH:29][N:28]3[N:30]=2)=[O:35])[CH2:37][CH2:38]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 5731761-methyl-1H-pyrazole-3-carboxylic acidHCID 57749401N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749202HCID 57749202, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 55 and using 1-methyl-1H-pyrazole-3-carboxylic acid (55.5 mg, 0.440 mmol), tetrahydrofuran (5 mL), thionyl chloride (77.0 μL, 0.888 mmol), N,N-dimethylformamide (2 drops), N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (129 mg, 0.399 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (100 mg, 58%) was obtained as a white solid.

Sources & evidence

ORD record
ord-7885d356b908470384b65207102f28df
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

Loading…