Tetrahydrofuran → HCID 57749282, compound

HRID 1874471Notes

Reaction equation

HRID 1874471 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.O1CCCC1.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:38]=[CH:39][C:40]=1[CH3:41])[O:22][C:23]1[CH:24]=[CH:25][C:26]2[N:27]([N:29]=[C:30]([NH:32][C:33]([CH:35]3[CH2:37][CH2:36]3)=[O:34])[N:31]=2)[CH:28]=1>CN(C)C=O.CN(C)C(=O)C>[CH:35]1([C:33]([NH:32][C:30]2[N:31]=[C:26]3[CH:25]=[CH:24][C:23]([O:22][C:21]4[CH:38]=[CH:39][C:40]([CH3:41])=[C:19]([NH:18][C:6]([CH:3]5[CH2:4][CH2:5][O:1][CH2:2]5)=[O:8])[CH:20]=4)=[CH:28][N:27]3[N:29]=2)=[O:34])[CH2:36][CH2:37]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 4661317(R)-Tetrahydro-3-furoic acidHCID 57749401N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749282HCID 57749282, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 55 and using tetrahydrofuran-3-carboxylic acid (57.0 mg, 0.491 mmol), tetrahydrofuran (5 mL), thionyl chloride (83.0 μL, 0.957 mmol), N,N-dimethylformamide (2 drops), N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (140 mg, 0.433 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (106 mg, 58%) was obtained as a white solid.

Sources & evidence

ORD record
ord-26814fe4078a4f08be7a212d2fb278c1
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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