Triethylamine → HCID 21467149, compound

HRID 2255984Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[C:10]3[S:16][CH:17]=[CH:18][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][C:29]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>C(Cl)Cl>[O:15]=[C:11]1[CH2:12][CH2:13][CH2:14][N:8]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:31](=[O:32])[C:30]3[CH:34]=[CH:35][CH:36]=[C:37]([F:38])[C:29]=3[CH3:28])=[CH:20][CH:19]=2)=[O:7])[C:9]2[CH:18]=[CH:17][S:16][C:10]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 287 mg of 4,5,6,7-tetrahydro-4-(4-aminobenzoyl)-8H-thieno[3,2-b]azepin-8-one in 3 ml of methylene chloride is added 209 μl of triethylamine which is cooled to 0° C. is added 207.1 mg of 2-methyl-3-fluorobenzoyl chloride. The cooling bath is removed and the reaction mixture stirred at room temperature under argon for 18 hours. An additional 50 ml of methylene chloride and 20 ml of water is added and the separated organic layer washed with 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried with Na2SO4 and passed through a short pad of hydrous magnesium silicate and the filtrate evaporated in vacuo to a white foam which is crystallized from ethyl acetate-hexane to give 305 mg of the desired product as a white solid, 200°-202° C.

Workup

customThe cooling bath is removed
additionAn additional 50 ml of methylene chloride and 20 ml of water is added
washthe separated organic layer washed with 2N citric acid, 1M NaHCO3 and brine
dry with materialThe organic layer is dried with Na2SO4
customthe filtrate evaporated in vacuo to a white foam which
customis crystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-36515d6b372a4b55b41edc495ba6e3fc
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654297

Reaction notes

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