1-Chloro-4-phenylphthalazine → HCID 66904277, compound

HRID 1689942Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[C:18]([N:25]1[CH2:30][C@@H:29]2[CH2:31][C@H:26]1[CH2:27][NH:28]2)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>ClCCl>[C:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([N:28]3[CH2:27][C@@H:26]4[CH2:31][C@H:29]3[CH2:30][N:25]4[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:3][N:4]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a 20 mL reaction vial was added 1-chloro-4-phenylphthalazine BSL-1 (300 mg, 1.25 mmol) and (1S,4S)-2-boc-2,5-diazabicyclo[2.2.1]heptane (494 mg, 2.5 mmol, 2 eq). The mixture was heated under nitrogen at 90° C. for 1 h. The reaction was cooled to room temperature and the solid mass was dissolved in dichloromethane (50 mL) and washed once with 5 mL of sat. NaHCO3 and once with 50 mL of sat. NaCl solution. The organic layer was dried over MgSO4, filtered, and concentrated. Purification by column chromatography (70% ethyl acetate in hexanes) afforded (1S,4S)-tert-butyl 5-(4-phenylphthalazin-1-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate (BSL-3). MS (M+H)+=403.1.

Workup

customTo a 20 mL reaction
temperatureThe reaction was cooled to room temperature
washwashed once with 5 mL of sat. NaHCO3 and once with 50 mL of sat. NaCl solution
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography (70% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-e0ffe7709c394d009d843115366f9ff0
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153633B2

Reaction notes

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