4-Methylcyclohexane-1-carbonyl chloride → 5-(3,3-dimethyl-but-1-ynyl)-3-[N-(4-methyl-cyclohexanecarbonyl)-N'-(2,2,2-trifluoro-acetyl)-hydrazino]-thiophene-2-carboxylic acid methyl ester

HRID 336049Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]#[C:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:8][C:9]=1[NH:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[O:4].[CH3:24][CH:25]1[CH2:30][CH2:29][CH:28]([C:31](Cl)=[O:32])[CH2:27][CH2:26]1>CN(C1C=CN=CC=1)C.ClCCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]#[C:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:8][C:9]=1[N:10]([C:31]([CH:28]1[CH2:29][CH2:30][CH:25]([CH3:24])[CH2:26][CH2:27]1)=[O:32])[NH:11][C:12](=[O:17])[C:13]([F:14])([F:15])[F:16])=[O:4]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 5-(3,3-dimethyl-but-1-ynyl)-3-[N′-(2,2,2-trifluoro-acetyl)-hydrazino]-thiophene-2-carboxylic acid methyl ester (2.1 g, 6.0 mmol), 4-methyl-cyclohexanecarbonyl chloride (1.45 g, 9 mmol), DMAP (1.1 g, 9 mmol) and DCE (20 mL) was heated to 40° C. for 16 h. After cooling, the mixture was concentrated and the product was purified by silica gel chromatography 0-30% EtOAc/hexanes to give 5-(3,3-dimethyl-but-1-ynyl)-3-[N-(4-methyl-cyclohexanecarbonyl)-N′-(2,2,2-trifluoro-acetyl)-hydrazino]-thiophene-2-carboxylic acid methyl ester (2.74 g, 5.8 mmol).

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated
customthe product was purified by silica gel chromatography 0-30% EtOAc/hexanes

Sources & evidence

ORD record: ord-59ca251ed45749eb83c843644ce27af0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884030B2

Reaction notes

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