Hydrochloric Acid → 2-[(2-chloro-1-oxobutyl)-amino]-beta-oxo-N-(2-pyridinyl)-3-trifluoromethyl benzene propanamide

HRID 231148Notes

Reaction equation

C([Li])CCC.[C:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)(=[O:8])[CH3:7].[Cl:16][CH:17]([C:20]1[O:25][C:24](=[O:26])[C:23]2[CH:27]=[CH:28][CH:29]=[C:30]([C:31]([F:34])([F:33])[F:32])[C:22]=2[N:21]=1)[CH2:18][CH3:19].Cl>CCCCCC.O1CCCC1.O>[Cl:16][CH:17]([CH2:18][CH3:19])[C:20]([NH:21][C:22]1[C:30]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](=[O:26])[CH2:7][C:6]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:8])=[O:25]

Participants

Conditions

Temperature: -70 °C

Procedure

314.3 ml of a 1.4M solution of n-butyllithium in hexane were added to a solution of 30 g of 2-acetylamino pyridine in 886 ml of tetrahydrofuran. After cooling to -70° C., a solution of 32 g of 2-(1-chloropropyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-one [prepared by the process of Example 10 of Belgian Pat. No. 896,941] in 230 ml of tetrahydrofuran was added and the solution was poured into 500 ml of 2N hydrochloric acid and 600 ml of water. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried and concentrated to dryness under reduced pressure. The residue was taken in ethyl ether, separated and dried to obtain 9.1 g of 2-[(2-chloro-1-oxobutyl)-amino]-β-oxo-N-(2-pyridinyl)-3-trifluoromethyl benzene propanamide melting at 137° C.

Workup

extractionThe aqueous phase was extracted with ethyl acetate
customthe combined organic phases were dried
concentrationconcentrated to dryness under reduced pressure
customseparated
customdried

Sources & evidence

ORD record: ord-f1b8df6c7c1e4d60a07074942dbb2c21
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845105

Reaction notes

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