Tetrahydrofuran → HCID 57749319, compound

HRID 1874452Notes

Reaction equation

HRID 1874452 reaction equation
[CH:1]([N:4]1[C:8]([C:9]([OH:11])=O)=[CH:7][C:6]([CH3:12])=[N:5]1)([CH3:3])[CH3:2].O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:24][C:25]1[CH:26]=[C:27]([CH:44]=[CH:45][CH:46]=1)[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:26]=[C:25]([NH:24][C:9]([C:8]5[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=[C:6]([CH3:12])[CH:7]=5)=[O:11])[CH:46]=[CH:45][CH:44]=4)=[CH:34][N:33]3[N:35]=2)=[O:40])[CH2:42][CH2:43]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 21877587HCID 21877587, compoundHCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749319HCID 57749319, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 18-4 and using 1-isopropyl-3-methyl-1H-pyrazole-5-carboxylic acid (218 mg, 1.29 mmol), tetrahydrofuran (7 mL), oxalyl chloride (169 μL, 1.94 mmol), N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.646 mmol), N,N-dimethylformamide (1 drop) and N,N-dimethylacetamide (3 mL) as starting materials, the title compound (264 mg, 89%) was obtained as a white solid.

Sources & evidence

ORD record
ord-f09fac68baa84535ade5ee65bfa2bca7
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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