Pyridine → HCID 53758202, compound

HRID 1826150Notes

Reaction equation

HRID 1826150 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].N1C=CC=CC=1.[NH2:16][C:17]1[C:31]([O:32][CH3:33])=[C:30]([CH3:34])[C:29]([O:35][CH3:36])=[CH:28][C:18]=1[C:19]([N:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[CH2:26][OH:27])=[O:20]>C(Cl)Cl>[CH3:34][C:30]1[C:29]([O:35][CH3:36])=[CH:28][C:18]([C:19]([N:21]2[CH2:25][CH2:24][CH2:23][CH:22]2[CH2:26][OH:27])=[O:20])=[C:17]([NH:16][C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3])[C:31]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 54431991HCID 54431991, compound

Product 1

HCID 53758202HCID 53758202, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2,2,2-trichloroethyl chloroformate (1.38 g, 6.5 mmol) in distilled DCM (25 mL) was added dropwise over 0.5 hours to a solution of anhydrous pyridine (1.03 g, 13 mmol) and 191 (1.91 g, 6.5 mmol) in distilled DCM (25 mL) at 0° C. After 6 hours at room temperature, the reaction mixture was diluted with anhydrous DCM (100 mL) and washed with 1 N HCl (2×100 mL), H2O (100 mL), brine (100 mL) and dried over anhydrous MgSO4. Evaporation of the solvent yielded a brown oil which was purified by flash column chromatography (silica gel, EtOAc) to afford the product (192) as a yellow glass (2.13 g, 4.53 mmol, 70%); 1H NMR (270 MHz, CDCl3) δ 7.59 (br s, 1H), 6.56 (s, 1H), 4.78 (br s, 2H), 4.25-4.23 (m, 1H), 3.82-3.79 (m, 3H+1H), 3.69-3.63 (m, 3H+1H), 3.52 (m, 1H), 3.42-3.33 (m, 1H), 2.13-2.06 (m, 3H+1H), 1.88-1.64 (m, 3H); 13C NMR (67.8 MHZ, CDCl3) δ 169.95, 156.82, 156.67, 154.02, 153.34, 131.92, 121.74, 119.33, 103.94, 95.43, 74.42, 66.04, 61.01, 60.60, 60.27, 55.73, 50.46, 28.53, 24.47, 9.13.

Workup

  1. washwashed with 1 N HCl (2×100 mL), H2O (100 mL), brine (100 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. customEvaporation of the solvent
  4. customyielded a brown oil which
  5. customwas purified by flash column chromatography (silica gel, EtOAc)

Sources & evidence

ORD record
ord-8ee0594ef13a47bd8bac02b737f7e24f
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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