Triethylamine → HCID 69780041, compound

HRID 841011Notes

Reaction equation

HRID 841011 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=O)[CH:11](Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([NH2:20])(=[S:19])[CH3:18].C(N(CC)CC)C>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[S:19][C:17]([CH3:18])=[N:20][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723949ThioacetamideHCID 59143774Tert-butyl 4-bromo-5-oxoazepane-1-carboxylate

Product 1

HCID 69780041HCID 69780041, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by the following reaction sequence: i) treatment of the 5-bromo-azepan-4-one hydrobromide (1:1) [Ger. Offen. (1989), DE 38207751] with di-t-butyldicarbonate in dioxane/aq. sodium hydrogen carbonate solution to yield the 4-bromo-5-oxo-azepane-1-carboxylic acid tert-butyl ester; ii) treatment of the 4-bromo-5-oxo-azepane-1-carboxylic acid tert-butyl ester with thioacetamide in ethanol in the presence of triethylamine at reflux to give the 2-methyl-4,5,7,8-tetrahydro-thiazolo[4,5-d]azepine-6-carboxylic acid tert-butyl ester; iii) conversion of the 2-methyl-4,5,7,8-tetrahydro-thiazolo[5-d]azepine-6-carboxylic acid tert-butyl ester into the 2-methyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine by removal of the tert-butyloxycarbonyl function with hydrogen chloride (aqueous, 37%) in methanol at room temperature.

Sources & evidence

ORD record
ord-357e6ce7d5104613b8acb53d8a0bc076
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

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