Diisopropylethylamine → HCID 178455879, compound

HRID 1978162Notes

Reaction equation

HRID 1978162 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@@H:8]([CH2:10][CH3:11])[NH2:9].Cl[C:13]1[CH:18]=[CH:17][NH:16][C:15](=[O:19])[C:14]=1[N+:20]([O-:22])=[O:21].C(N(CC)C(C)C)(C)C>CC(O)C>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@H:8]([NH:9][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([OH:19])[C:14]=1[N+:20]([O-:22])=[O:21])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5192824-Chloro-3-nitro-1,2-dihydropyridin-2-one2×HCID 11041539(R)-3-chloro-alpha-ethyl-2-thiopheneethanamine2×

Product 1

HCID 178455879HCID 178455879, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 3-neck 1 liter round bottom flask fitted with a mechanical stirrer, thermocouple, nitrogen inlet and a condenser is sequentially charged: 14.5 g of (R)-3-chloro-a-ethyl-2-thiopheneethanamine (Compound III), 10.9 grams of 4-chloro-3-nitropyridin-2(1H)-one (Compound II), 35 grams of 2-propanol (IPA) and 25 mL of N,N-diisopropylethylamine (DIPEA). The mixture is stirred at 70° C.±2° C. for 7 hours before the reaction is allowed to cool overnight to room temperature (22° C±3° C.). The mixture is concentrated to 41. 4 g. of a syrup which is subsequently dissolved in 425 ml of ethyl acetate. This solution is washed with 125 mL of water, 2×50 mL of 5N ammonium chloride solution and 2×50 mL of saturated sodium chloride solution before drying over sodium sulfate. The solution is filtered, concentrated, and the resulting solid collected by filtration to give Compound IV, m.p. 150-152° C. Mass Spec. (EI), m/z 328 (6%), 1HNMR (500 Mhz, DMSO) δ 0.91 (3H, t); 1.8-1.6 (2H, m); 3.1 (1H, m); 3.95 (1H, m); 5.9 (1H, d); 7.0 (1H, d); 7.3 (1H, dd); 7.5 (1H, d); 8.8 (1H, d); 11.1 (1H).

Workup

  1. customTo a 3-neck 1 liter round bottom flask fitted with a mechanical stirrer
  2. additionthermocouple, nitrogen inlet and a condenser is sequentially charged
  3. temperatureto cool overnight to room temperature (22° C±3° C.)
  4. concentrationThe mixture is concentrated to 41
  5. dissolutionof a syrup which is subsequently dissolved in 425 ml of ethyl acetate
  6. washThis solution is washed with 125 mL of water, 2×50 mL of 5N ammonium chloride solution and 2×50 mL of saturated sodium chloride solution
  7. dry with materialbefore drying over sodium sulfate
  8. filtrationThe solution is filtered
  9. concentrationconcentrated
  10. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-16a75823ceb04f8bb3748e43efb25174
Source dataset
uspto-grants-2001_05
Patent number
US06235909B1

Reaction notes

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