Potassium Carbonate → 2-(6-Bromophthalazin-1-yl)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane

HRID 2357575Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.Cl.Cl.[CH:15]([N:18]1[CH2:23][CH:22]2[CH2:24][CH:19]1[CH2:20][NH:21]2)([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:21]1[CH2:20][CH:19]3[CH2:24][CH:22]1[CH2:23][N:18]3[CH:15]([CH3:17])[CH3:16])=[N:7][N:6]=[CH:5]2

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 6-bromo-1-chlorophthalazine (Example 1, 90 mg, 370 μmol), 2-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane dihydrochloride (95 mg, 444 μmol) and potassium carbonate (153 mg, 1109 μmol) in 10 mL acetonitrile was stirred at 130° C. under in a sealed tube. The mixture turned red in about 5 min. The reaction was monitored by MS. After about 1 h at 130° C., MS and TLC showed all starting material was converted to product (M+1=347, 349). The mixture was cooled down to room temperature, and concentrated on a Rotavaporator. After purification by column (eluting with gradient of 2-10% 2M ammonia in methanol to DCM), 2-(6-bromophthalazin-1-yl)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane (60 mg) was obtained as a yellow solid.

Workup

waitAfter about 1 h at 130° C.
temperatureThe mixture was cooled down to room temperature
concentrationconcentrated on a Rotavaporator
customAfter purification
washby column (eluting with gradient of 2-10% 2M ammonia in methanol to DCM)

Sources & evidence

ORD record: ord-fd80c4107ed34b238a174c7c744eabdc
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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