Chlorosuccinimide → HCID 89726263, compound

HRID 1777735Notes

Reaction equation

HRID 1777735 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=[O:12])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C1C(=O)N([Cl:21])C(=O)C1>CC#N>[Cl:21][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:1]([CH2:10][C:11]([OH:13])=[O:12])[CH:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22139374(1H-Pyrrolo[2,3-b]pyridin-1-yl)acetic acid

Product 1

HCID 89726263HCID 89726263, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 2-(1H-pyrrolo[2,3-b]pyridin-1-yl)acetic acid (100 mg) in MeCN (10 mL) was added NCS (91 mg) and the reaction mixture was stirred at 60° C. overnight and at 65° C. for 20 h. The solvent was removed in vacuo, the residue was taken up in DCM and the resulting precipitate was filtered off. The precipitate was further washed with DCM and dried in vacuo. 92 mg of grey solid was obtained. LC-MS (B): tR=0.66 min; [M+H]+: 211.02.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationthe resulting precipitate was filtered off
  3. washThe precipitate was further washed with DCM
  4. customdried in vacuo

Sources & evidence

ORD record
ord-239a59c217984798aad5e05da56dbf7a
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

Loading…