HCID 19917098, compound → HCID 19917109, compound

HRID 1464797Notes

Reaction equation

HRID 1464797 reaction equation
BrCC1N=C([C:8](OCC)=[O:9])SC=1.BrCCC1ON=C(C(OCC)=O)C=1.BrCC1N=C(C(OCC)=O)OC=1.[CH2:38]([N:40]([CH2:51][C:52]1[N:53]=[C:54]([CH2:57][OH:58])SC=1)[CH2:41]/[CH:42]=[CH:43]/[C:44]#[C:45][C:46]([O:49][CH3:50])([CH3:48])[CH3:47])[CH3:39].C(N(CC1ON=C(CO)C=1)C/C=C/C#CC(OC)(C)C)C>>[CH2:38]([N:40]([CH2:51][C:52]1[O:58][C:57]([CH2:8][OH:9])=[CH:54][N:53]=1)[CH2:41]/[CH:42]=[CH:43]/[C:44]#[C:45][C:46]([O:49][CH3:50])([CH3:48])[CH3:47])[CH3:39]

Participants

6

Reactant 5

HCID 19917098HCID 19917098, compoundHCID 19917117HCID 19917117, compoundHCID 19917122HCID 19917122, compoundHCID 19917136HCID 19917136, compoundHCID 57134191HCID 57134191, compound

Product 1

HCID 19917109HCID 19917109, compound

Procedure

When the same reactions as in Referential Example 49 are carried out using ethyl 4-bromomethylthiazol-2-carboxylate [see Ann., 1981, 623] or ethyl 5-bromoethylisoxazol-3-carboxylate [synthesized by brominating ethyl 5-methylisoxazole-5-carboxylate [see J. Heterocyclic Chem., 19, 557(1982)] with N-bromosuccimide in carbon tetrachloride] insted of the starting ethyl 4-bromomethyloxazol-2-carboxylate, (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-2 -hydroxymethyl-4-thiazolylmethylamine and (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-3-hydroxymethyl-5-isoxazolylmethylamine are obtained.

Workup

  1. customare obtained

Sources & evidence

ORD record
ord-e3a7bee4148a45ec894b6b2466eb71a0
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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