Tetrahydrofuran → HCID 57749339, compound

HRID 1874528Notes

Reaction equation

HRID 1874528 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([C:8]([OH:10])=O)[N:7]=1)[CH3:2].O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:26][C:27]1[CH:28]=[C:29]([CH:46]=[CH:47][CH:48]=1)[O:30][C:31]1[CH:32]=[CH:33][C:34]2[N:35]([N:37]=[C:38]([NH:40][C:41]([CH:43]3[CH2:45][CH2:44]3)=[O:42])[N:39]=2)[CH:36]=1>CN(C)C=O.CN(C)C(=O)C>[CH:43]1([C:41]([NH:40][C:38]2[N:39]=[C:34]3[CH:33]=[CH:32][C:31]([O:30][C:29]4[CH:28]=[C:27]([NH:26][C:8]([C:6]5[N:7]=[C:3]([CH2:1][CH3:2])[O:4][C:5]=5[C:11]([F:14])([F:13])[F:12])=[O:10])[CH:48]=[CH:47][CH:46]=4)=[CH:36][N:35]3[N:37]=2)=[O:42])[CH2:44][CH2:45]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamideHCID 57749173HCID 57749173, compound

Product 1

HCID 57749339HCID 57749339, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 18-4 and using 2-ethyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic acid (314 mg, 1.50 mmol), tetrahydrofuran (7 mL), oxalyl chloride (143 μL, 1.65 mmol), N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (309 mg, 1.00 mmol), N,N-dimethylformamide (1 drop) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (244 mg, 49%) was obtained as a white solid.

Sources & evidence

ORD record
ord-558c083dd00544b081aca91b54875733
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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