Triethylamine → HCID 67365908, compound

HRID 619818Notes

Reaction equation

HRID 619818 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[C:4]1=[O:17].C(N(CC)CC)C.[N:25]1[C:34]2[C:29](=[CH:30][C:31]([S:35](Cl)(=[O:37])=[O:36])=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>CC#N.CCOC(C)=O>[C:12]([C:11]1[CH:10]=[C:9]([CH:16]=[CH:15][CH:14]=1)[CH2:8][N:5]1[CH2:6][CH2:7][C@H:3]([NH:2][S:35]([C:31]2[CH:30]=[C:29]3[C:34](=[CH:33][CH:32]=2)[N:25]=[CH:26][CH:27]=[CH:28]3)(=[O:36])=[O:37])[C:4]1=[O:17])#[N:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12386743Quinoline-6-sulfonyl chlorideHCID 228707863-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride

Product 1

HCID 67365908HCID 67365908, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride (0.32 g, 1.26 mmol) is suspended in 15 mL of CH3CN. To the solution is added triethylamine (0.384 g, 3.78 mmol) followed by quinoline-6-sulfonyl chloride (0.25 g, 0.99 mmol). After stirring for 1.5 hours, the solution is diluted with EtOAc and washed with 0.1 N aqueous HCl, water and saturated NaCl solution. The organic layer is dried over Na2SO4, filtered and concentrated. The crude residue is purified by column chromatography (4% MeOH/CH2Cl2) to afford the title compound (0.146 g, 0.36 mmol) and as a solid.

Workup

  1. washwashed with 0.1 N aqueous HCl, water and saturated NaCl solution
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue is purified by column chromatography (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-95672efe918c4cc48b86ad7d90b7ba7f
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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