Hydrochloric Acid → HCID 86596761, compound

HRID 2105293Notes

Reaction equation

HRID 2105293 reaction equation
[CH3:1][C:2]1[C:8]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:7]([CH3:14])[CH:6]=[C:5]([CH3:15])[C:3]=1[NH2:4].N1C=CC=CC=1.[C:22]1([S:28]([N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[C:36](Cl)=[O:37])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>ClCCl>[C:22]1([S:28]([N:31]2[CH2:35][CH2:34][CH2:33][C@H:32]2[C:36]([NH:4][C:3]2[C:5]([CH3:15])=[CH:6][C:7]([CH3:14])=[C:8]([N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[C:2]=2[CH3:1])=[O:37])(=[O:29])=[O:30])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 107982512,4,6-Trimethyl-3-(pyrrolidin-1-yl)anilineHCID 12547433HCID 12547433, compound

Product 1

HCID 86596761HCID 86596761, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 2,4,6-trimethyl-3-pyrrolidin-1-ylaniline (220 mg, 1.00 mmol) in of anhydrous dichloromethane (20 mL), were added pyridine (0.100 mL, 1.3 mmol) and 1-benzenesulfonyl-pyrrolidine-2-carbonyl chloride (0.297 g, 1.0 mmol). The reaction mixture was stirred overnight at room temperature. The solution was acidified with HCl (1N, 20 mL) and extracted with CH2Cl2 (2×20 mL). The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate (10 mL) and dried over magnesium sulfate (MgSO4). The organic layers were filtered and concentrated under reduced pressure to give a brown solid. The residue was further purified by flash chromatography (silica gel) using 95-5% hexane/ethyl acetate as the mobile phase (gradient) and semi-preparative HPLC to give ′1-(Phenylsulfonyl)-N-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)prolinamide (157 mg) as an off-white solid. MS m/z (M+H)+: calculated (m/z) 442.22, found (m/z) 442.25.

Workup

  1. extractionextracted with CH2Cl2 (2×20 mL)
  2. washThe combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate (10 mL)
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. filtrationThe organic layers were filtered
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown solid
  7. customThe residue was further purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-3e0e924396ea4019b2ccaf9ff0d90086
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

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