Triethylamine → HCID 22727110, compound

HRID 2086278Notes

Reaction equation

HRID 2086278 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]2[CH:6]=[C:7]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([NH:19][CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:15](=[O:26])[CH2:14]3)(=[O:12])=[O:11])[CH2:8][O:9][C:4]=2[CH:3]=1.Cl.Cl[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[CH:28]=[CH:27][C:5]2[CH:6]=[C:7]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([NH:19][CH:20]4[CH2:25][CH2:24][N:23]([C:31]5[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=5)[CH2:22][CH2:21]4)[C:15](=[O:26])[CH2:14]3)(=[O:11])=[O:12])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 22727289HCID 22727289, compound

Product 1

HCID 22727110HCID 22727110, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Method B) A mixture of 4-(7-bromo-2H-benzopyran-3-sulfonyl)-1-(4-piperidinylamino)-2-piperazinone (471 mg), 4-chloropyridine hydrochloride (225 mg) and triethylamine (405 mg) in ethanol (20 ml) was reacted in a sealed tube at 150° C. for 18 hours. The reaction mixture was concentrated, and the residue was made alkaline by adding a saturated aqueous solution of sodium hydrogen carbonate, and then extracted with dichloromethane. The extract was washed with water and brine, dried and concentrated to obtain a residue, which was purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=12:1) and crystallized from a mixture of ethanol and diethyl ether to obtain the title compound (156 mg) as colorless crystals.

Workup

  1. customwas reacted in a sealed tube at 150° C. for 18 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionby adding a saturated aqueous solution of sodium hydrogen carbonate
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customto obtain a residue, which
  9. customwas purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=12:1)
  10. customcrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-028609785bde49a98f64366d3825dc86
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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