Triethylamine → HCID 16223018, compound

HRID 856987Notes

Reaction equation

HRID 856987 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:10]2[N:14]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[Cl:20])[O:12][N:11]=2)[CH:6]=[CH:7][C:8]=1[Cl:9].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.CCN(CC)CC>ClCCl>[Cl:9][C:8]1[CH:7]=[CH:6][C:5]([C:10]2[N:14]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][C:19]=3[Cl:20])[O:12][N:11]=2)=[CH:4][C:3]=1[CH2:2][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 16223016HCID 16223016, compound

Product 1

HCID 16223018HCID 16223018, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(3-bromomethyl-4-chloro-phenyl)-5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol (0.030 g, 0.077 mmol), pyrrolidine (0.013 mL, 0.16 mmol), Et3N (0.054 mL, 0.39 mmol) and dichloromethane (8.0 mL) was stirred at room temperature for 20 h. The solution was diluted with dichloromethane (30 mL), washed with 10% Na2CO3 (25 mL), dried over Na2SO4, and concentrated. The product was azeotroped with dichloromethane (3×5 mL) and hexanes (2×5 mL) to give 0.028 g (96%) of the title compound as a white solid. 1H NMR (CDCl3): 8.27 (d, 1H, J=1.7 Hz), 7.98 (dd, 1H, J=8.2 and 1.9 Hz), 7.61 (d, 1H, J=5.2 Hz), 7.49 (d, 1H, J=8.5 Hz), 7.13 (d, 1H, J=5.2 Hz), 3.85 (s, 2H), 2.67 (br s, 4H), 1.84 (br s, 4H).

Workup

  1. washwashed with 10% Na2CO3 (25 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was azeotroped with dichloromethane (3×5 mL) and hexanes (2×5 mL)

Sources & evidence

ORD record
ord-5809e74271794a9bb8ac6c4aa663086e
Source dataset
uspto-grants-2006_12
Patent number
US07144876B2

Reaction notes

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