Tetrahydrofuran → HCID 57749184, compound

HRID 1874469Notes

Reaction equation

HRID 1874469 reaction equation
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([OH:10])=O.O1CCCC1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:22]=[C:23]([CH:40]=[CH:41][C:42]=1[CH3:43])[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>[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([NH:20][C:21]1[CH:22]=[C:23]([O:24][C:25]2[CH:26]=[CH:27][C:28]3[N:29]([N:31]=[C:32]([NH:34][C:35]([CH:37]4[CH2:38][CH2:39]4)=[O:36])[N:33]=3)[CH:30]=2)[CH:40]=[CH:41][C:42]=1[CH3:43])=[O:10]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 46169203-chloro-4-methylthiophene-2-carboxylic acidHCID 57749401N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749184HCID 57749184, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 55 and using 3-chloro-4-methylthiophene-2-carboxylic acid (90.0 mg, 0.510 mmol), tetrahydrofuran (5 mL), thionyl chloride (89.0 μL, 1.02 mmol), N,N-dimethylformamide (2 drops), N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.464 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (174 mg, 78%) was obtained as a pale-yellow solid.

Sources & evidence

ORD record
ord-a91fbd2b70a5401cb8a5f829d3aea708
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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