Hydrochloric Acid → (R)-N,N-dimethyl-2-(5-(1-methylpyrrolidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)ethanamine dihydrochloride

HRID 241676Notes

Reaction equation

HRID 241676 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@@H:17]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25].[ClH:29].C(OCC)(=O)C>C(O)C>[ClH:29].[ClH:29].[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@@H:17]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18]3)(=[O:15])=[O:16])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:23][C:24]([CH3:26])([CH3:25])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 46851890(R)-N,N-dimethyl-2-(5-(1-methylpyrrolidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)ethanamine

Product 1

HCID 46851889(R)-N,N-dimethyl-2-(5-(1-methylpyrrolidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)ethanamine dihydrochlorideYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)—N,N-dimethyl-2-(5-(1-methylpyrrolidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)ethanamine (STEP D, 419 mg, 1.03 mmol) was dissolved in ethanol (2 mL). To the resulting solution was added 4 mol/L hydrogen chloride in ethyl acetate solution (502 microL, 2.01 mmol) at room temperature. The whole was concentrated in vacuo. The resulting solid was recrystallized from a mixture of ethanol (5 mL) and ethyl acetate (1.5 mL) to give the title compound (177 mg, 36%).

Workup

  1. concentrationThe whole was concentrated in vacuo
  2. customThe resulting solid was recrystallized from a mixture of ethanol (5 mL) and ethyl acetate (1.5 mL)

Sources & evidence

ORD record
ord-40a80f7f481f4dfaae8e4459890f1fa8
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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