HCID 178418546, compound → HCID 178461998, compound

HRID 46148Notes

Reaction equation

[C:1]([Cu])#[N:2].Br[C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]2[S:15][C:16]([CH3:24])([C:20]([F:23])([F:22])[F:21])[C:17](=[O:19])[N:18]=2)[CH3:12])=[CH:7][CH:6]=1>CN(C=O)C>[CH3:24][C:16]1([C:20]([F:23])([F:22])[F:21])[S:15][C:14]([NH:13][C@H:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]#[N:2])=[CH:6][CH:7]=2)[CH3:12])=[N:18][C:17]1=[O:19]

Participants

Conditions

Temperature: 150 °C

Procedure

CuCN (140 mg, 1.6 mmol) and 2-((S)-1-(4-bromophenyl)ethylamino)-5-methyl-5-(trifluoromethyl)thiazol-4(5H)-one (150 mg, 0.39 mmol) and 2 mL of DMF were combined in a sealed tube and heated to 150° C. for 12 h. The residue was purified by column chromatography (10 to 60% EA/Hex, 40 g) to give 4-((S)-1-(5-methyl-4-oxo-5-(trifluoromethyl)-4,5-dihydrothiazol-2-ylamino)ethyl)benzonitrile as a slightly yellow solid.

Workup

customThe residue was purified by column chromatography (10 to 60% EA/Hex, 40 g)

Sources & evidence

ORD record: ord-613611c01263454da4cf48ed541ed53d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541592B2

Reaction notes

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