Triethylamine → HCID 57941484, compound

HRID 1437889Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][C@@:9]12[C:15]([CH3:17])([CH3:16])[C@@H:12]([CH2:13][CH2:14]1)[CH:11]([C:18](Cl)=[O:19])[C:10]2=[O:21].[C:22]([O:26][C:27]([NH:29][NH:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[Cl:38])=[O:28])([CH3:25])([CH3:24])[CH3:23]>ClCCl>[C:22]([O:26][C:27]([NH:29][N:30]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[Cl:38])[C:18]([CH:11]1[C:10](=[O:21])[C@:9]2([CH3:8])[C:15]([CH3:17])([CH3:16])[C@H:12]1[CH2:13][CH2:14]2)=[O:19])=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (3.9 mL; 28 mmol) was added over a period of 2-3 min to a cooled (0° C.) solution of (1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl chloride (Intermediate 25; 2.2 g, 10.2 mmol) in dichloromethane (25 mL), resulting in a heavy precipitate. Dichloromethane (10 mL) was added, followed by N′-(2-chloro-4-fluoro-phenyl)-hydrazinecarboxylic acid tert-butyl ester (Intermediate 33; 1.87 g, 7.2 mmol). The reaction mixture was stirred at 0° C. for 5 min, and then at 50° C. (oil-bath temperature) over the weekend. Dichloromethane was added and the solution was washed with water (3×50 mL) and brine (50 mL), dried (magnesium sulfate, filtered, evaporated, and dried under high vacuum to give N′-(2-chloro-4-fluoro-phenyl)-N′-((1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (3.8 g, 120% of the expected amount). This was used directly in the next step without further purification.

Workup

customresulting in a heavy precipitate
customat 50° C.
washthe solution was washed with water (3×50 mL) and brine (50 mL)
dry with materialdried (magnesium sulfate
filtrationfiltered
customevaporated
customdried under high vacuum

Sources & evidence

ORD record: ord-dfeec86f69be41cb994eb26940be37b6
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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