Triethylamine → HCID 23205191, compound

HRID 1975985Notes

Reaction equation

HRID 1975985 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([NH:13][C:14](=[O:30])[CH2:15][NH:16][S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)(=[O:19])=[O:18])[C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].C(N(CC)CC)C.[N:38]1[CH:43]=[CH:42][C:41]([N:44]2[CH2:49][CH2:48][CH:47]([C:50](Cl)=[O:51])[CH2:46][CH2:45]2)=[CH:40][CH:39]=1>C(Cl)Cl>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[S:17]([NH:16][CH2:15][C:14]([NH:13][CH:4]([C:5]([N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:6])[CH2:3][NH:2][C:50]([CH:47]1[CH2:46][CH2:45][N:44]([C:41]2[CH:40]=[CH:39][N:38]=[CH:43][CH:42]=2)[CH2:49][CH2:48]1)=[O:51])=[O:30])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111837001-(4-Pyridinyl)-4-piperidinecarbonyl chlorideHCID 22721828HCID 22721828, compound

Product 1

HCID 23205191HCID 23205191, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2-Amino-1-(piperidinocarbonyl)ethyl]-2-(2-naphthalene-sulphonamido)acetamide hydrochloride salt (2.6 g) and triethylamine (3.18 ml) were added in turn to a stirred solution of 1-(4-pyridyl)piperidine-4-carbonyl chloride (1.54 g) in methylene chloride (20 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 89:10:1 mixture of ethyl acetate, methanol and ammonia as eluent. The material so obtained was triturated under diethyl ether to give 2-(2-naphthalenesulphonamido)-N-{1-piperidinocarbonyl-2-[1-(4-pyridyl)-piperidin-4-ylcarbonylamino]ethyl}acetamide as a foam (1.9 g, 55%);

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. additiona 89:10:1 mixture of ethyl acetate, methanol and ammonia as eluent
  7. customThe material so obtained
  8. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-2e65e25a955b48e6b524daaa87c63e80
Source dataset
uspto-grants-2001_05
Patent number
US06225309B1

Reaction notes

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