1,1'-Carbonyldiimidazole → HCID 178461348, compound
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([NH2:31])[CH2:27][CH2:26]1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([NH:31][C:8](=[O:10])[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=2)[CH2:27][CH2:26]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of 6-bromopicolinic acid acid (3 g, 14.85 mmol), and 1,1′-carbonyldiimidazole (2.41 g, 14.85 mmol) in dimethylformamide (30 mL) was heated at 50° C. for 2 hours. After this time, trans-4-methylcyclohexylamine hydrochloride (2.2 g, 14.85 mmol), and N,N-diisopropylethylamine (3.88 mL, 22.3 mmol) were added and the mixture heated at 50° C. for 16 hours. The reaction mixture was cooled, and diluted with ethyl acetate (300 mL). The organic solution was washed with water (4×300 mL). The aqueous extracts were washed with ethyl acetate (2×250 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated. Chromatography of the crude product through a Biotage silica cartridge (15×4 cm i.d.) using ethyl acetate—hexane (1:3, containing 1% diethylamine) afforded 3.84 g (87%) of 409:
Workup
- temperatureThe reaction mixture was cooled
- washThe organic solution was washed with water (4×300 mL)
- washThe aqueous extracts were washed with ethyl acetate (2×250 mL)
- dry with materialThe combined organic extracts were dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-992e38995df6402f86e349f57cf0782c
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06429207B1
Reaction notes
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