(4-Tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine → N-(4-tert-butylbenzyl)-2-chloro-N-[2-(3,4-dichlorophenyl)-ethyl]-3-fluoro-6-methylaminobenzamide

HRID 2244378Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:10](=[O:12])OC(=O)[N:7]([CH3:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:15].[C:16]([C:20]1[CH:37]=[CH:36][C:23]([CH2:24][NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.C(OCC)(=O)C>[C:16]([C:20]1[CH:37]=[CH:36][C:23]([CH2:24][N:25]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[C:10](=[O:12])[C:11]2[C:6]([NH:7][CH3:14])=[CH:5][CH:4]=[C:3]([F:15])[C:2]=2[Cl:1])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 5-chloro-6-fluoro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (83 mg, 0.36 mmol) and (4-tert-butylbenzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine (122 mg, 0.36 mmol) in DMF (2 ml) was heated to 140° C. for 2 h and then at 110° C. overnight. The reaction mixture was then cooled to RT and the mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give the desired product (51 mg, 27%) as a white solid. MS (ISP) 521.9 (M+H)+.

Workup

customat 110° C.
customovernight
temperatureThe reaction mixture was then cooled to RT
washwashed with water and brine
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give a residue which
customwas purified by flash column chromatography

Sources & evidence

ORD record: ord-852e110b28ee4bfc94e3a55108dd8d44
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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