1-Acetylpiperazine → 1-{4-[3-(8-Chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)cyclobutyl]piperazin-1-yl}ethanone

HRID 1640569Notes

Reaction equation

HRID 1640569 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:15][C:14](=O)[CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:31]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)(=[O:33])[CH3:32]>ClCCCl>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:15][CH:14]([N:37]4[CH2:38][CH2:39][N:34]([C:31](=[O:33])[CH3:32])[CH2:35][CH2:36]4)[CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 837951-AcetylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 16743592HCID 16743592, compound

Product 1

HCID 576809621-{4-[3-(8-Chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)cyclobutyl]piperazin-1-yl}ethanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Into a RBF 3-(8-chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)cyclobutanone (1.00 g, 0.0029 mol) and sodium triacetoxyborohydride (1.30 g, 0.006 mol) were dissolved in 1,2-dichloroethane (65.0 mL) and a solution of 1-acetylpiperazine (0.39 g, 0.003 mol) in 1,2-dichloroethane was added to the reaction. The reaction mixture was stirred at rt for 2 h. The crude product was concentrated in vacuo and the dissolved in CH2Cl2 (25.0 mL) and washed with saturated NaHCO3 solution (1×40 mL). The product was dried with sodium sulfate and concentrated in vacuo to yield a light yellow solid; MS (ES+): m/z 459.84 (100) [MH+], 461.80 (40) [MH+++]; HPLC: tR=1.81 min (OpenLynx, polar—5 min); 1H NMR (CDCl3, 400 MHz) δ 2.04-2.15 (m, 3 H) 2.26-2.50 (m, 6 H) 2.55-2.72 (m, 2 H) 2.83-2.99 (m, 1 H) 3.29-3.52 (m, 3 H) 3.56-3.67 (m, 2 H) 7.29 (d, 1 H) 7.58 (d, 1 H).

Workup

  1. concentrationThe crude product was concentrated in vacuo
  2. dissolutionthe dissolved in CH2Cl2 (25.0 mL)
  3. washwashed with saturated NaHCO3 solution (1×40 mL)
  4. dry with materialThe product was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield a light yellow solid
  7. customMH+++]; HPLC: tR=1.81 min (OpenLynx, polar—5 min)

Sources & evidence

ORD record
ord-a18090de8ddb4845815afb93d2b21bde
Source dataset
uspto-grants-2012_02
Patent number
US08114846B2

Reaction notes

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