Sodium Azide → HCID 90134933, compound

HRID 1483037Notes

Reaction equation

HRID 1483037 reaction equation
CS(O[CH2:6][CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[NH:8]1)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C>[N:18]([CH2:6][CH:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[NH:8]1)=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 90134931HCID 90134931, compound

Product 1

HCID 90134933HCID 90134933, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve (1-oxo-3,4-dihydro-2H-isoquinolin-3-yl)methyl methanesulfonate (3 g, 11.7 mmol) in DMF (10 mL). Add NaN3; heat to 70° C. and stir overnight. Concentrate under reduced pressure; add water; and extract with EtOAc. Combine the extracts and remove the solvents under reduced pressure to provide the title compound (1.7 g, 71.5%). 1H NMR (400 mHz, CDCl3): δ 8.1 (s, 1H), 7.6 (m, 1H), 7.5 (m, 1H), 7.0 (s, 1H), 3.9 (m, 1H), 3.5 (m, 2H), 3.0 (m, 2H).

Workup

  1. concentrationConcentrate under reduced pressure
  2. extractionand extract with EtOAc
  3. customremove the solvents under reduced pressure

Sources & evidence

ORD record
ord-009d029518d145d1b681008c41288516
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

Loading…