Bromoacetonitrile → HCID 118598909, compound

HRID 1050419Notes

Reaction equation

HRID 1050419 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[C:15](=[O:16])[N:14]3[C:17]4([NH:23][C:24](=[O:25])[C:13]3=[C:12]([CH3:26])[CH:11]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:4]=1[O:27][CH3:28].[CH:29]([N:32](CC)C(C)C)(C)[CH3:30].BrCC#N>CN(C)C=O.[Cl-].[NH4+]>[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[C:15](=[O:16])[N:14]3[C:17]4([NH:23][C:24](=[O:25])[C:13]3=[C:12]([CH3:26])[CH:11]=2)[CH2:22][CH2:21][N:20]([CH2:30][C:29]#[N:32])[CH2:19][CH2:18]4)[C:4]=1[O:27][CH3:28]

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 118598679HCID 118598679, compound

Product 1

HCID 118598909HCID 118598909, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

6-((6-Amino-5-methoxypyrimidin-4-yl)amino)-8-methyl-2H-spiro[imidazo[1,5-a]pyridine-3,4′-piperidine]-1,5-dione hydrochloride (5, 0.18 g, 0.44 mmol) was dissolved in dimethylformamide (5 mL). To this mixture N,N-diisopropylethylamine (0.23 g, 1.76 mmol) was added followed by bromoacetonitrile (79 mg, 0.66 mmol). The reaction mixture was stirred at room temperature for 2 h. After completion the reaction mixture was diluted with saturated ammonium chloride solution (50 mL). Yellow precipitate was filtered and dried under reduced pressure. The compound was then purified by prep purification to afford 2-(6-((6-amino-5-methoxypyrimidin-4-yl)amino)-8-methyl-1,5-dioxo-1,5-dihydro-2H-spiro[imidazo[1,5-a]pyridine-3,4′-piperidin]-1′-yl)acetonitrile (Cpd. No. 243) as white solid. Yield: 40 mg, 22%; MS (ESI) m/z 411.20 [M+1]+; 1H NMR (400 MHz, DMSO-d6 with d1-TFA) δ 8.37 (s, 1H), 8.27 (s, 1H), 4.49 (s, 2H), 3.76 (s, 3H), 3.74-3.71 (m, 2H), 3.56-3.40 (m, 4H), 2.43 (s, 3H), 1.90-1.87 (m, 2H).

Workup

  1. filtrationYellow precipitate was filtered
  2. customdried under reduced pressure
  3. customThe compound was then purified by prep purification

Sources & evidence

ORD record
ord-8c38962f96cf44a8b888be8ca45aa303
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…