Hydrochloric Acid → HCID 22479270, compound

HRID 2182622Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:16](=[O:17])[CH:15]3[N:11]([CH2:12][CH2:13][CH2:14]3)[C:10]2=[O:18])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Li+].CC([N-]C(C)C)C.[Li]CCCC.C(NC(C)C)(C)C.[C:39]([C:41]1[CH:48]=[CH:47][C:44]([CH:45]=[O:46])=[CH:43][CH:42]=1)#[N:40].Cl>C1COCC1>[C:39]([C:41]1[CH:48]=[CH:47][C:44]([CH:45]([C:15]23[CH2:14][CH2:13][CH2:12][N:11]2[C:10](=[O:18])[N:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:16]3=[O:17])[OH:46])=[CH:43][CH:42]=1)#[N:40]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-(3,5-dichlorophenyl)-1,3-diazabicyclo[3.3.0]octane-2,4-dione, (5.63 g) in anhydrous THF (20 mL) at −78° C. was added LDA prepared from n-BuLi (13.6 mL) and diisopropylamine (3.33 mL). The reaction mixture was stirred at −78° C. for 30 minutes then at 0° C. for 1 hour. To this mixture was added in one portion 4-cyanobenzaldehyde (3.64 g). The reaction mixture was allowed to warm to room temperature for 3 hours then poured onto 1 N HCl (50 mL). The mixture was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered and the solvent evaporated. The residue was purified by chromatography (SiO2, hexanes to 1:1 hexanes/EtOAc gradient elution) and HPLC (18C-Waters 40×210 mm, 1% HOAc/CH3CN gradient) to provide the titled product (5.5 g). MS (m/z) 416 (MH+); mp. 184.4° C.

Workup

waitat 0° C. for 1 hour
temperatureto warm to room temperature for 3 hours
extractionThe mixture was extracted with EtOAc
dry with materialthe combined organic layers were dried over Na2SO4
filtrationfiltered
customthe solvent evaporated
customThe residue was purified by chromatography (SiO2, hexanes to 1:1 hexanes/EtOAc gradient elution) and HPLC (18C-Waters 40×210 mm, 1% HOAc/CH3CN gradient)

Sources & evidence

ORD record: ord-ff7fb9a09e804b5785260fffaac1f73b
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897225B1

Reaction notes

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