Bromoacetonitrile → HCID 118598704, compound

HRID 1050418Notes

Reaction equation

HRID 1050418 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[Cl:27].[CH:28]([N:31](CC)C(C)C)(C)[CH3:29].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]([CH2:29][C:28]#[N:31])[CH2:19][CH2:18]4)[C:4]=1[Cl:27]

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 118598632HCID 118598632, compound

Product 1

HCID 118598704HCID 118598704, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

6-((6-Amino-5-chloropyrimidin-4-yl)amino)-8-methyl-2H-spiro[imidazo[1,5-a]pyridine-3,4′-piperidine]-1,5-dione hydrochloride (5, 75 mg, 0.20 mmol) was dissolved in dimethylformamide (5 mL). To this mixture N,N-diisopropylethylamine (77 mg, 0.60 mmol) and bromoacetonitrile (36 mg, 0.30 mmol) were added. The reaction mixture was stirred at room temperature for 2 h. After completion reaction mixture was diluted with saturated ammonium chloride solution (50 mL). The yellow precipitate out was filtered and dried under reduced pressure. The crude was purified by prep purification to afford 2-(6-((6-amino-5-chloropyrimidin-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. 238) as white solid. Yield: 14 mg, 17%; MS (ESI) m/z 414.85 [M+1]+; 1H NMR (400 MHz, DMSO-d6 with d1-TFA) δ 8.49 (s, 1H), 8.33 (s, 1H), 4.49 (s, 2H), 3.76-3.71 (m, 2H), 3.58-3.41 (m, 4H), 2.42 (s, 3H), 1.90-1.87 (m, 2H).

Workup

  1. customAfter completion reaction mixture
  2. filtrationThe yellow precipitate out was filtered
  3. customdried under reduced pressure
  4. customThe crude was purified by prep purification

Sources & evidence

ORD record
ord-c61e8eb89237491d88602b2c3e33a9e0
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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