4-Methylmorpholine → HCID 67995913, compound

HRID 2042904Notes

Reaction equation

HRID 2042904 reaction equation
[S:1]1[C:5]([C:6](O)=O)=[CH:4][N:3]=[CH:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)[N:27]=[N:26][C:24]=2C=1.CN1CCOCC1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1>>[S:46]1[CH:24]=[N:26][N:27]=[C:6]1[C:5]1[S:1][CH:2]=[N:3][CH:4]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 84494Thiazole-5-carboxylic acidHCID 87949Lawesson's reagent

Product 1

HCID 67995913HCID 67995913, compoundYield 44%

Procedure

The ester or 1,3,4-thiadiazole substituted thiazoles at ring B may be prepared as shown in Scheme 12. Typical conversion of the carboxylic acid 55 to amide functionality via acyl chloride and the following thionation using Lawesson's reagent produce the corresponding thioamide, which is treated with ethyl 2-chloro-2-formylacetate and pyridine in refluxed ethanol to provide the corresponding thiazole-5-carboxylic acid 56 in 35% over four steps. The ester 56 is hydrolysed under basic conditions to generate the corresponding acid. Next, this acid is coupled with formyl hydrazide under conditions of EDCI, HOBt, and NMM. Following cyclization using Lawesson's reagent produced 5-(1,3,4-thiadiazol-2-yl)-thiazole 57 in 44% yield for the four steps.

Sources & evidence

ORD record
ord-ae798df560394740adb261f0fb096eac
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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