Phosphorus pentachloride → 2-Cyclopropylamino-4-methyl-thiazole-5-carboxylic acid (cyano-furan-2-yl-methyl)-amide

HRID 439294Notes

Reaction equation

HRID 439294 reaction equation
[CH:1]1([NH:4][C:5]2[S:6][C:7]([C:11]([OH:13])=O)=[C:8]([CH3:10])[N:9]=2)[CH2:3][CH2:2]1.C1(NC2SC(C(Cl)=O)=C(C)N=2)CC1.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[NH2:34][CH:35]([C:38]1[O:39][CH:40]=[CH:41][CH:42]=1)[C:36]#[N:37]>C(N(CC)CC)C>[C:36]([CH:35]([NH:34][C:11]([C:7]1[S:6][C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[N:9][C:8]=1[CH3:10])=[O:13])[C:38]1[O:39][CH:40]=[CH:41][CH:42]=1)#[N:37]

Participants

6

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 13075762HCID 13075762, compoundHCID 224110622-(Cyclopropylamino)-4-methyl-1,3-thiazole-5-carboxylic acidHCID 544544602-Cyclopropylamino-4-methyl-thiazole-5-carboxylic acid chloride

Product 1

HCID 544634362-Cyclopropylamino-4-methyl-thiazole-5-carboxylic acid (cyano-furan-2-yl-methyl)-amideYield 38.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.4g of 2-cyclopropylamino-4-methyl-thiazole-5-carboxylic acid was converted into 2-cyclopropylamino-4-methyl-thiazole-5-carboxylic acid chloride using 1.6g of phosphorus pentachloride according to the same procedure as EXAMPLE 1. Then 1.2g of amino-furan-2-yl-acetonitrile hydrochloride and 3.2ml of triethylamine were added thereto and the reaction mixture was treated according to the same procedure as EXAMPLE 1 to obtain 0.83g (Yield 35%) of the title compound.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-ef0b9783dd61415194e92ee385f16e06
Source dataset
uspto-grants-1996_05
Patent number
US05514643

Reaction notes

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