Triethylamine → HCID 16222399, compound

HRID 2250461Notes

Reaction equation

HRID 2250461 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]=[C:12]([C:14]3[S:15][CH:16]=[CH:17][C:18]=3[Cl:19])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.Br[CH2:28][C:29](Br)=[O:30].[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>O1CCCC1.C(O)C.ClCCl>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:13]=[C:12]([C:14]3[S:15][CH:16]=[CH:17][C:18]=3[Cl:19])[O:11][N:10]=2)=[CH:3][C:2]=1[NH:1][C:29](=[O:30])[CH2:28][N:36]1[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 61147Bromoacetyl bromideHCID 99956372-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine

Product 1

HCID 16222399HCID 16222399, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(3-amino-4-chloro-phenyl)-5-(3-chlorothiophen-2-yl)-[1,2,4]-oxadiazole (56.5 mg, 0.181 mmol), triethylamine (75.0 μL, 0.540 mmol), and bromo-acetyl bromide (48.0 μL, 0.549 mmol) and dichloromethane (15.0 mL) was stirred at room temperature for 30 min. The solution was washed with 5% hydrochloric acid solution, dried over sodium sulfate, and rotary evaporated to dryness. To the residue was added ethanol (10 mL), tetrahydrofuran (10 mL), and 1-methyl-piperazine (525 μL, 4.73 mmol) and the resulting solution was refluxed for 20 min under argon. The solution was partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate (15 mL). The ethyl acetate layer was washed with water (15 mL), dried over sodium sulfate and rotary evaporated to dryness to yield 68.7 mg (84%) of the title compound as a white solid. 1H NMR (CDCl3): 10.04 (s, 1H), 9.25 (d, J=1.92 Hz, 1H), 7.85 (dd, J1=8.24 Hz, J2=1.64 Hz, 1H), 7.60 (d, J=5.22 Hz, 1H), 7.52 (d, J=8.24 Hz, 1H), 7.12 (d, J=5.49 Hz, 1H), 3.24 (s, 2H), 2.73 (s, 4H), 2.57 (s, 4H), 2.35 (s, 3H).

Workup

  1. washThe solution was washed with 5% hydrochloric acid solution
  2. dry with materialdried over sodium sulfate
  3. customrotary evaporated to dryness
  4. temperaturethe resulting solution was refluxed for 20 min under argon
  5. customThe solution was partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate (15 mL)
  6. washThe ethyl acetate layer was washed with water (15 mL)
  7. dry with materialdried over sodium sulfate
  8. customrotary evaporated to dryness

Sources & evidence

ORD record
ord-b68d6801e6e24e3888c45aef33c1d496
Source dataset
uspto-grants-2008_01
Patent number
US07317029B2

Reaction notes

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