Tetrahydrofuran → HCID 57749123, compound

HRID 1874521Notes

Reaction equation

HRID 1874521 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:42]=[CH:43][CH:44]=1)[O:26][C:27]1[N:32]=[C:31]2[S:33][C:34]([NH:36][C:37]([CH:39]3[CH2:41][CH2:40]3)=[O:38])=[N:35][C:30]2=[CH:29][CH:28]=1>CN(C)C=O.CN(C)C(=O)C>[CH:39]1([C:37]([NH:36][C:34]2[S:33][C:31]3[C:30]([N:35]=2)=[CH:29][CH:28]=[C:27]([O:26][C:25]2[CH:24]=[C:23]([NH:22][C:8]([C:3]4[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=4)=[O:10])[CH:44]=[CH:43][CH:42]=2)[N:32]=3)=[O:38])[CH2:40][CH2:41]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 2687573-Methylpicolinic acidHCID 57387081HCID 57387081, compound

Product 1

HCID 57749123HCID 57749123, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 18-4 and using 3-methylpyridine-2-carboxylic acid (132 mg, 0.965 mmol), tetrahydrofuran (8 mL), oxalyl chloride (169 μL, 1.93 mmol), N-[5-(3-aminophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (210 mg, 0.643 mmol), N,N-dimethylformamide (1 drop) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (220 mg, 77%) was obtained as a white solid.

Sources & evidence

ORD record
ord-bdbfb0348fa946f9a605fc336f5f1d96
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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