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

HRID 439292Notes

Reaction equation

HRID 439292 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:12]([OH:14])=O)=[C:9]([CH3:11])[N:10]=1)=[O:4].COC(NC1SC(C(Cl)=O)=C(C)N=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[NH2:36][CH:37]([C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)[C:38]#[N:39]>C(N(CC)CC)C>[C:38]([CH:37]([NH:36][C:12]([C:8]1[S:7][C:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])=[N:10][C:9]=1[CH3:11])=[O:14])[C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)#[N:39]

Participants

6

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 133524562-Thiopheneacetonitrile, a-amino-, monohydrochlorideHCID 224110642-Methoxycarbonylamino-4-methyl-thiazole-5-carboxylic acidHCID 540625992-Methoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid chloride

Product 1

HCID 545158552-Methoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl)-amideYield 32.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.7g of 2-methoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid was converted into 2-methoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid chloride using 1.8g of phosphorus pentachloride according to the same procedure as EXAMPLE 1. Then 1.5g of amino-thiophen-2-yl-acetonitrile hydrochloride and 2.4ml of triethylamine were added thereto and the reaction mixture was treated according to the same procedure as EXAMPLE 1 to obtain 0.85g (Yield 32%) of the title compound.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-bb809b9696024e2887f4202f6cf519b4
Source dataset
uspto-grants-1996_05
Patent number
US05514643

Reaction notes

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