Chlorosuccinimide → HCID 24773647, compound

HRID 645384Notes

Reaction equation

HRID 645384 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Cl:20]N1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O>ClCCl.O>[F:19][C:2]([F:18])([F:1])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[C:13]([Cl:20])=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 62406Trifluoromethanesulfonic acidHCID 86613107HCID 86613107, compound

Product 1

HCID 24773647HCID 24773647, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (S)-N-Trifluoroacetyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.62 g, 2.1 mmol) in dichloromethane (10 mL) was treated with N-chlorosuccinimide (0.284 g, 2.1 mmol) and trifluoromethanesulfonic acid (0.639 g, 4.2 mmol). The reaction was stirred for 16 h at 20° C., diluted with water (20 mL) and extracted with dichloromethane (25 mL). The organics were dried with MgSO4, filtered and concentrated. HPLC purification was done to provide 0.078 g of a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 7.32-7.25 (m, 1H), 6.97-6.93 (m, 1H), 4.27-4.24 (m, 0.6H), 4.19-4.13 (m, 1H), 4.08-4.01 (m, 1H), 3.91-3.86 (0.8H, m), 3.74-3.69 (m, 0.8H:), 3.45-3.37 (m, 1H), 3.31-3.21 (m, 1H), 2.96-2.80 (m, 1H), 1.28-1.22 (m, 3H). MS calculated for C13H12Cl2F3NO+H: 326, observed: 326.

Workup

  1. extractionextracted with dichloromethane (25 mL)
  2. dry with materialThe organics were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customHPLC purification

Sources & evidence

ORD record
ord-3dfebf32e06443f5843e79e43dff5a51
Source dataset
uspto-grants-2010_04
Patent number
US07704993B2

Reaction notes

Loading…