3-[(3-Amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride → HCID 54067569, compound

HRID 2759Notes

Reaction equation

HRID 2759 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=2[OH:17])[C:12]#[N:13])[C:4]1=[O:18].[Cl:19][C:20]1[C:28]2[CH:27]=[C:26]([S:29](Cl)(=[O:31])=[O:30])[S:25][C:24]=2[CH:23]=[C:22]([Cl:33])[CH:21]=1>N1C=CC=CC=1>[OH:17][C:16]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[CH2:8][N:5]1[CH2:6][CH2:7][CH:3]([NH:2][S:29]([C:26]2[S:25][C:24]3[CH:23]=[C:22]([Cl:33])[CH:21]=[C:20]([Cl:19])[C:28]=3[CH:27]=2)(=[O:31])=[O:30])[C:4]1=[O:18]

Participants

4

Reactant 2

HCID 193509103-[(3-Amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochlorideHCID 19350936HCID 19350936, compound

Product 1

HCID 54067569HCID 54067569, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride (0.20 g, 0.75 mmol) in 3 mL of pyridine at 0° C. is added 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The solution is allowed to warm to ambient temperatures and is stirred for 6 h. After this time, the solution is concentrated. The residue is dissolved in CH2 Cl2. The organic solution is washed with 1N HCl and saturated NaCl. The crude product is triturated with Et2O to give the title compound (0.22 g, 0.44 mmol) as a white solid.

Workup

  1. temperatureto warm to ambient temperatures
  2. concentrationAfter this time, the solution is concentrated
  3. dissolutionThe residue is dissolved in CH2 Cl2
  4. washThe organic solution is washed with 1N HCl and saturated NaCl
  5. customThe crude product is triturated with Et2O

Sources & evidence

ORD record
ord-8e6bf9e4d5934b93a925c96b54265e92
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Reaction notes

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