Triethylamine → 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-[4-methoxycarbonyl-1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinone

HRID 1840561Notes

Reaction equation

HRID 1840561 reaction equation
Cl.[Cl:2][C:3]1[CH:33]=[CH:32][C:6]2[CH:7]=[C:8]([S:11]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4([C:27]([O:29][CH3:30])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[C:16](=[O:31])[CH2:15]3)(=[O:13])=[O:12])[CH2:9][O:10][C:5]=2[CH:4]=1.Cl.Cl[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C(N(CC)CC)C>C(O)C>[Cl:2][C:3]1[CH:33]=[CH:32][C:6]2[CH:7]=[C:8]([S:11]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4([C:27]([O:29][CH3:30])=[O:28])[CH2:26][CH2:25][N:24]([C:40]5[CH:39]=[CH:38][N:37]=[CH:36][CH:41]=5)[CH2:23][CH2:22]4)[C:16](=[O:31])[CH2:15]3)(=[O:13])=[O:12])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 156199202-Chloropyridine--hydrogen chloride (1/1)HCID 234475944-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone hydrochloride

Product 1

HCID 234475694-(7-chloro-2H-benzopyran-3-sulfonyl)-1-[4-methoxycarbonyl-1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinoneYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-[1-(tert-butoxycarbonyl)-4-methoxycarbonylpiperidin-4-ylmethyl]-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone (260 mg) was added 4N hydrochloric acid in ethyl acetate (10 ml) and methanol (4 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated to give colorless solid of 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone hydrochloride (228 mg). A solution of 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone hydrochloride (228 mg), chloropyridine hydrochloride (80 mg) and triethylamine (225 mg) in ethanol (14 ml) was allowed to react in a sealed tube at 150% for 15 hours. The reaction solution was concentrated, and the residue was dissolved in dichloromethane. The solution was washed with 1N sodium hydroxide solution, dried and concentrated, and the residue was purified with silica gel column chromatography (dichloromethane:methanol containing 10% ammonia solution=20:1) to give colorless solid of the title compound (126 mg).

Workup

  1. customto react in a sealed tube at 150% for 15 hours
  2. concentrationThe reaction solution was concentrated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe solution was washed with 1N sodium hydroxide solution
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified with silica gel column chromatography (dichloromethane:methanol containing 10% ammonia solution=20:1)

Sources & evidence

ORD record
ord-41baa1fc51954319abe5bde20498c2d2
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

Loading…