Hydrochloric Acid → 2-Oxo-3-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile hydrochloride

HRID 2064096Notes

Reaction equation

HRID 2064096 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C.[Cl:32][C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl.ClC(Cl)C.Cl>O1CCOCC1>[ClH:32].[O:35]=[C:33]1[NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N:10]1[CH:11]1[CH2:12][CH2:13][N:14]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:15][CH2:16]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 691227084-Amino-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}-benzonitrile

Product 1

HCID 691226462-Oxo-3-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Amino-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}benzonitrile (D59, 240 mg, 0.0008 mol, 1 eq), diisopropylethylamine (140 mg, 0.00104 mol, 1.3 eq), triphosgene (70 mg, 0.00024 mol, 0.3 eq), and dichloroethane (20 ml) were combined. After 5 min, 4 ml of 4M HCl in dioxane were added, the reaction evaporated, the residue dissolved in methanol and purified exactly as in Example 1, where A=H2O and B=CH3CN to produce the title compound as a white solid. MS (ESI): 327 [M+H]+.

Workup

  1. customthe reaction evaporated
  2. dissolutionthe residue dissolved in methanol
  3. custompurified exactly as in Example 1, where A=H2O and B=CH3CN

Sources & evidence

ORD record
ord-6de1f0dc22d24e3e9fb3692d28c4ab09
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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