Hydrochloric Acid → HCID 67407492, compound

HRID 1622192Notes

Reaction equation

HRID 1622192 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH2:13]1)[CH3:10].[ClH:29]>C(O)(C)(C)C>[ClH:29].[ClH:29].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH2:13]1)[CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58973516HCID 58973516, compound

Product 1

HCID 67407492HCID 67407492, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 54 mg of 4-[(S)-3-aminopyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide and 30 mg of 2-methoxyacetophenone in 1 ml of THF was added 85 mg of titanium isopropoxide, and the mixture was stirred at room temperature for 1 day. Further, 12 mg of sodium borohydride was added to the reaction mixture, and then, 0.3 ml of methanol was added to the mixture, and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added 0.5 ml of 28% aqueous ammonia solution, the mixture was stirred, and then, insoluble materials were removed and the solvent was evaporated. The residue was purified by LC/MS to obtain 61 mg of 4-[(S)-3-[1-(2-methoxyphenyl)ethylamino]pyrrolidin-1-yl]-N,N-dimethyl-benzene sulfonamide. The 4-[(S)-3-[1-(2-methoxyphenyl)ethylamino]pyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide was dissolved by adding 1 ml of tert-butanol, 0.15 ml of 2M aqueous hydrochloric acid was added thereto, and after stirring the mixture, it was freeze-dried to obtain 4-[(S)-3-[1-(2-methoxyphenyl)ethylamino]pyrrolidin-1-yl]-N,N-dimethyl-benzenesulfonamide dihydrochloride (the following Table Y, Example 13.001).

Workup

  1. additionwas added
  2. customwas freeze-dried

Sources & evidence

ORD record
ord-866580f04d6d4046b0c511101f4605f7
Source dataset
uspto-grants-2014_07
Patent number
US08778628B2

Reaction notes

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