Tetrahydrofuran → HCID 57749322, compound

HRID 1874449Notes

Reaction equation

HRID 1874449 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:22]=[C:23]([CH:40]=[CH:41][CH:42]=1)[O:24][C:25]1[CH:26]=[CH:27][C:28]2[N:29]([N:31]=[C:32]([NH:34][C:35]([CH:37]3[CH2:39][CH2:38]3)=[O:36])[N:33]=2)[CH:30]=1>CN(C)C=O.CN(C)C(=O)C>[CH:37]1([C:35]([NH:34][C:32]2[N:33]=[C:28]3[CH:27]=[CH:26][C:25]([O:24][C:23]4[CH:22]=[C:21]([NH:20][C:6]([C:4]5[N:3]=[CH:2][O:1][CH:5]=5)=[O:8])[CH:42]=[CH:41][CH:40]=4)=[CH:30][N:29]3[N:31]=2)=[O:36])[CH2:38][CH2:39]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 142814301,3-Oxazole-4-carboxylic acidHCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749322HCID 57749322, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 18-4 and using 1,3-oxazole-4-carboxylic acid (146 mg, 1.29 mmol), tetrahydrofuran (10 mL), oxalyl chloride (168 μL, 1.93 mmol), N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.647 mmol), N,N-dimethylformamide (2 drops) and N,N-dimethylacetamide (10 mL) as starting materials, the title compound (120 mg, 46%) was obtained as a white solid.

Sources & evidence

ORD record
ord-f66cbd76a837463db37a80b9518f24f5
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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