Potassium Carbonate → HCID 118598732, compound
Reaction equation
Cl[C:2]1[CH:7]=C(NC2N=CN=C(NC(C3CC3)=O)C=2)C(=O)[N:4]2C(C3C=CC=C(F)C=3)(C)NC(=O)[C:3]=12.C(=O)([O-])[O-].[K+].[K+].Cl.[Br:41][C:42]1[C:47](=[O:48])[N:46]2[C:49]3([NH:55][C:56](=[O:57])[C:45]2=[C:44]([Cl:58])[CH:43]=1)[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3>C(#N)C>[Br:41][C:42]1[C:47](=[O:48])[N:46]2[C:49]3([NH:55][C:56](=[O:57])[C:45]2=[C:44]([Cl:58])[CH:43]=1)[CH2:54][CH2:53][N:52]([CH2:7][CH2:2][C:3]#[N:4])[CH2:51][CH2:50]3Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A flask was charges with 6-bromo-8-chloro-spiro[2H-imidazo[1,5-a]pyridine-3,4′-piperidine]-1,5-dione hydrochloride (1, 0.5 g, 1.35 mmol) and acetonitrile (15 mL) was added. The reaction mass was cooled to 0° C. and potassium carbonate (281 mg, 2.03 mmol) was added followed by addition of 2-bromoacetonitrile (2, 218 mg, 1.63 mmol). The reaction mass was stirred at room temperature for 10 h. After completion, the solvent was removed under reduced pressure to get the crude. The crude was purified by Biotage snap using 1-3% methanol in dichloromethane. The desired fractions were concentrated to get 3-(6-bromo-8-chloro-1,5-dioxo-spiro[2H-imidazo[1,5-a]pyridine-3,4′-piperidine]-1′-yl)propanenitrile (3) as brown solid. Yield: 0.42 g, 83%; MS (ESI) m/z 373.18 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 10.83 (s, 1H), 8.25 (s, 1H), 3.75 (s, 2H), 3.15-3.10 (m, 2H), 2.87-2.72 (m, 2H), 2.66-2.60 (m, 2H) 1.57-1.54 (m, 2H).
Workup
- customA flask was
- customAfter completion, the solvent was removed under reduced pressure
- customto get the crude
- customThe crude was purified by Biotage snap
- concentrationThe desired fractions were concentrated
Sources & evidence
- ORD record
- ord-be8b8349d2834607a311fc5709d0128d
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382248B2
Reaction notes
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