1,1'-Carbonyldiimidazole → HCID 68671615, compound

HRID 2047396Notes

Reaction equation

HRID 2047396 reaction equation
C1N=CN(C(N2C=NC=C2)=[O:7])C=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][C:15]=1[C:26]1[NH:30][C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[N:27]=1.[CH:35]([N:38]([CH2:42]C)[CH:39](C)C)(C)[CH3:36]>C(#N)C>[NH:30]1[C:29]2[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=2[N:27]=[C:26]1[C:15]1[CH:16]=[C:17]([N:20]2[CH2:25][CH2:24][N:23]([C:36](=[O:7])[CH2:35][N:38]([CH3:42])[CH3:39])[CH2:22][CH2:21]2)[CH:18]=[CH:19][C:14]=1[F:13]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 68670575HCID 68670575, compound

Product 1

HCID 68671615HCID 68671615, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

CDI (0.052 g, 0.32 mmol) was added to a solution of N,N-dimethylglicine (0.033 g, 0.32 mmol) in acetonitrile (2.50 mL). The resulting solution was stirred at room temperature for 5 hours. Then 2-(2-Fluoro-5-piperazin-1-yl-phenyl)-1H-benzoimidazole (0.10 g, 0.27 mmol) and N,N-diisopropylethylamine (DIPEA) (0.11 mL, 0.6 mmol) were added and reaction was heated at 65° C. overnight. Reaction was cooled to room temperature and solvent was removed under reduced pressure. DCM (2 mL) was added to the crude, organic solution was washed with water (2×4 mL) and with saturated Na2CO3 solution (2×4 mL) and concentrated. The crude reaction mixture was purified by flash chromatography (eluent: MeOH:AcOEt gradient from 100% of AcOEt to MeOH 0.6:AcOEt 4) to afford 0.049 g of the title compound (43%).

Workup

  1. customreaction
  2. temperaturewas heated at 65° C. overnight
  3. customReaction
  4. temperaturewas cooled to room temperature
  5. customsolvent was removed under reduced pressure
  6. additionDCM (2 mL) was added to the crude, organic solution
  7. washwas washed with water (2×4 mL) and with saturated Na2CO3 solution (2×4 mL)
  8. concentrationconcentrated
  9. customThe crude reaction mixture
  10. customwas purified by flash chromatography (eluent: MeOH:AcOEt gradient from 100% of AcOEt to MeOH 0.6:AcOEt 4)

Sources & evidence

ORD record
ord-2e98b52a76da4aecbf685e4f7f4a3aaf
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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