1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 71093128, compound

HRID 876372Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH:15]([F:17])[F:16])[CH2:13][CH2:12][O:11][C:10]([NH2:14])=[N:9]2)[CH:7]=1.Cl[C:20]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.C(OCC)(=O)C.CCCCCCC>ClCCl>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([C:20]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[NH:14][C:10]2[O:11][CH2:12][CH2:13][C@:8]([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[F:18])([CH:15]([F:16])[F:17])[N:9]=2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of (S)-4-(5-bromo-2-fluorophenyl)-4-(difluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (intermediate E6.1) (372 mg, 1.15 mmol) in dichloromethane (10 ml) was added at 0° C. 4,4′-(chloro(phenyl)methylene)bis(methoxybenzene) (585 mg, 1.73 mmol). The reaction mixture was stirred at 23° C. for 16 hours. Extraction with water, then drying of the organic layer over Na2SO4, filtration, evaporation. Chromatography on 20 g silica gel with ethyl acetate/heptane 0-50% gave the (S)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-4-(5-bromo-2-fluorophenyl)-4-(difluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (725 mg, 1.1 mmol, 95.6% yield) as a white foam. MS (ISP): m/z=625.2 [M+H]+ and 627.3 [M+2+H]+.

Workup

extractionExtraction with water
dry with materialdrying of the organic layer over Na2SO4, filtration, evaporation

Sources & evidence

ORD record: ord-cc4a5680b3254cb0a29e78e0d3b00a99
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987255B2

Reaction notes

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