Triethylamine → HCID 59486212, compound

HRID 1949172Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH2:39]([S:41][C:42]1[C:51]([C:52](O)=[O:53])=[C:50]([CH3:55])[C:49]2[C:44](=[CH:45][C:46]([C:56]([F:59])([F:58])[F:57])=[CH:47][CH:48]=2)[N:43]=1)[CH3:40]>C1COCC1.CCCCCC>[CH2:39]([S:41][C:42]1[C:51]([C:52]([NH:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:53])=[C:50]([CH3:55])[C:49]2[C:44](=[CH:45][C:46]([C:56]([F:59])([F:57])[F:58])=[CH:47][CH:48]=2)[N:43]=1)[CH3:40]

Participants

Conditions

Temperature: 50 °C

Procedure

134 μl (1.3 mmol) thiophenemethanamine, 438 mg (1.1 mmol) HATU and 420 μl (3.0 mmol) NEt3 were added in succession to a solution of 330 mg (1.05 mmol) 2-(ethylthio)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid (VVV08) in THF (8 ml) and the mixture was then heated for 24 h at 50° C. Then it was diluted with EE and washed with a 4M aqueous NH4Cl solution, a 1M aqueous Na2CO3 solution and brine. The organic phase was dried over MgSO4 and then filtered through a silica layer. Column chromatography (hexane/EE 7:3) of the residue yielded 277 mg (0.67 mmol, 65%) 2-ethylsulfanyl-4-methyl-N-(thiophen-2-yl-methyl)-7-(trifluoromethyl)-quinoline-3-carboxamide. MS: m/z 411.1 [M+H]+.

Workup

additionThen it was diluted with EE
washwashed with a 4M aqueous NH4Cl solution
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered through a silica layer

Sources & evidence

ORD record: ord-12b53aa9a3dd4806ad4e23a92b26d7f1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399673B2

Reaction notes

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