Pyridine → HCID 90082733, compound

HRID 1771971Notes

Reaction equation

HRID 1771971 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[NH:12][CH2:13][CH2:14][NH:15]3)=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:26](Cl)([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[NH:12][CH2:13][CH2:14][N:15]2[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 90082926HCID 90082926, compound

Product 1

HCID 90082733HCID 90082733, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-chlorophenyl)(1,2,3,4-tetrahydroquinoxalin-5-yl)methanone (50 g, 183 mmol) in DCM (200 mL) at 0° C. was added pyridine (17.79 mL, 220 mmol). Then CBZ—Cl (26.2 mL, 183 mmol) in DCM (1.0 mL) was added dropwise. The reaction mixture was warmed up to room temperature and stirred at room temperature for 3 h. The reaction mixture was washed with H2O, saturated NaHCO3, and brine, dried over Na2SO4, filtered, concentrated to give crude material. This crude material was purified via BIOTAGE®, eluted with 10% EtOAC/hexane to afford benzyl 5-(3-chlorobenzoyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate, Intermediate E-1D (60 g, 147 mmol, 80% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.5 (1H, bs), 7.6 (1H, s), 7.45 (2H, m), 7.4 (7H, m), 7.25 (1H, m), 6.5 (1H, m), 5.2 (2H, m), 3.9 (2H, m), 3.6 (2H, m).

Workup

  1. washThe reaction mixture was washed with H2O, saturated NaHCO3, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude material
  6. customThis crude material was purified via BIOTAGE®
  7. washeluted with 10% EtOAC/hexane

Sources & evidence

ORD record
ord-80e2d568636943c0a03c51658928fdec
Source dataset
uspto-grants-2016_02
Patent number
US09249157B2

Reaction notes

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