Sodium Chloride → HCID 178490111, compound

HRID 1443231Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)=[CH:4][C:3]=1[O:19][CH3:20].[NH2:21][C:22]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]2[C:23]=1[CH:24]=[N:25][C:26]([CH3:33])=[N:27]2.[Cl-].[Na+].[CH3:36]C1C=CC=CC=1C>[Ti+4]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:18])([CH3:36])[CH2:9][C:10](/[CH:11]=[N:21]/[C:22]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]3[C:23]=2[CH:24]=[N:25][C:26]([CH3:33])=[N:27]3)([OH:17])[C:13]([F:14])([F:15])[F:16])=[CH:4][C:3]=1[O:19][CH3:20]

Participants

Conditions

Temperature: 120 °C

Procedure

350 mg (1.08 mmol) of (rac.)-4-(4-chloro-3-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)-pentanal is mixed in 5.8 ml of o-xylene with 190.9 mg (1.08 mmol) of 5-amino-8-fluoro-2-methylquinazoline. After 0.64 ml (2.16) of titanium(IV) isopropylate is added, it is refluxed for three hours (bath temperature 120° C.). After cooling, the batch is added to saturated sodium chloride solution and stirred vigorously for 20 minutes. After being extracted twice with ethyl acetate, the combined organic extracts are washed with brine. After drying on sodium sulfate, suctioning off the dessicant and spinning off the solvent, the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 327.5 mg (62.8%) of the desired imine is isolated.

Workup

temperatureAfter cooling
extractionAfter being extracted twice with ethyl acetate
washthe combined organic extracts are washed with brine
customAfter drying on sodium sulfate
customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

Sources & evidence

ORD record: ord-c55f90018301403abfefb6056a0b2806
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659297B2

Reaction notes

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