Triethylamine → HCID 59750900, compound

HRID 748852Notes

Reaction equation

HRID 748852 reaction equation
C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]([NH:27][NH2:28])=[O:26].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([CH:39]([C:49]2[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:50]=2[F:56])[C:40]2[N:45]=[CH:44][C:43]([C:46](O)=[O:47])=[CH:42][CH:41]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1>CN(C)C1C=CN=CC=1.ClCCl.ClCCl.CCCCCC>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]([NH:27][NH:28][C:46](=[O:47])[C:43]1[CH:42]=[CH:41][C:40]([CH:39]([S:36]([C:33]2[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=2)(=[O:37])=[O:38])[C:49]2[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:50]=2[F:56])=[N:45][CH:44]=1)=[O:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 187312-Furancarboxylic acid, hydrazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23114724[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid

Product 1

HCID 59750900HCID 59750900, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 21226440Methylenechloride HexaneSolvent

Procedure

Triethylamine (32 μl, 0.23 mmol), 4-dimethylaminopyridine (12 mg, 0.095 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (44 mg, 0.23 mmol) and 2-furancarboxylic acid hydrazide (29 mg, 0.23 mmol) were added to a solution of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (80 mg, 0.19 mmol), which had been obtained in Example 338, in dichloromethane (5 ml). The resulting mixture was stirred at room temperature for 7.5 hours. The reaction mixture was diluted with dichloromethane, followed by successive washing with water, a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel colunm and a fraction obtained from the elution portion with dichloromethane:methanol=50:1 was concentrated under reduced pressure. The solid thus obtained was recrystallized from dichloromethane-hexane, whereby the title compound (58 mg, 0.11 mmol, 58%) was obtained as a white powder.

Workup

  1. washby successive washing with water
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customa fraction obtained from the elution portion with dichloromethane
  6. concentrationmethanol=50:1 was concentrated under reduced pressure
  7. customThe solid thus obtained

Sources & evidence

ORD record
ord-9909b842e22843dfa1be547b9d500dc5
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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