Hydrochloric Acid → HCID 69026917, compound

HRID 1433033Notes

Reaction equation

HRID 1433033 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:11]=[C:10]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[NH:24][C:23]4[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:22]=4[N:21]=3)[CH2:15][C:14]2=[O:30])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[C:31](#[N:33])[CH3:32]>O1CCOCC1>[NH2:7][C:6]1[C:5]2[C:4](=[CH:11][C:10]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([CH2:19][C:20]4[NH:24][C:23]5[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:22]=5[N:21]=4)[CH2:15][C:14]3=[O:30])=[CH:9][CH:8]=2)[N:3]=[C:31]([CH3:32])[N:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 69027088HCID 69027088, compound

Product 1

HCID 69026917HCID 69026917, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stream of hydrogen chloride gas is bubbled intermittently through an ice-cold mixture of 2-amino-4-[4-(6-chloro-1H-benzoimidazol-2-ylmethyl)-2-oxo-piperidin-1-ylmethyl]-benzonitrile hydrochloric acid salt (57 mg, 0.123 mmol), EXAMPLE 814, Part E, and acetonitrile (0.03 mL, 0.93 mmol) in 1.5 mL of dioxane for six hours. The dioxane is removed; the residue is purified by reverse phase HPLC (0-40% ACN/H2O). The desired product (9.5 mg, 12% yield) is isolated as a clear wax. C23H23ClN6O MS m/z: 435, 437.

Workup

  1. customThe dioxane is removed
  2. customthe residue is purified by reverse phase HPLC (0-40% ACN/H2O)

Sources & evidence

ORD record
ord-869d650f81c7445cb001295a7fc3723d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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