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

HRID 1636777Notes

Reaction equation

HRID 1636777 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 hours. After this time, the solution is concentrated. The residue is dissolved in CH2Cl2. The organic solution is washed with 1 N 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 CH2Cl2
  4. washThe organic solution is washed with 1 N HCl and saturated NaCl
  5. customThe crude product is triturated with Et2O

Sources & evidence

ORD record
ord-5446542fe23c4ac1856f4c616269aadf
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Reaction notes

Loading…