Triethylamine → 6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-N-cyclohexylmethylnicotinamide

HRID 748850Notes

Reaction equation

HRID 748850 reaction equation
C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[NH2:20][CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH:38]([C:48]2[CH:53]=[C:52]([F:54])[CH:51]=[CH:50][C:49]=2[F:55])[C:39]2[N:44]=[CH:43][C:42]([C:45](O)=[O:46])=[CH:41][CH:40]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH:38]([C:48]2[CH:53]=[C:52]([F:54])[CH:51]=[CH:50][C:49]=2[F:55])[C:39]2[CH:40]=[CH:41][C:42]([C:45]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:46])=[CH:43][N:44]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 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 231146576-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-N-cyclohexylmethylnicotinamideYield 59%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

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 aminomethylcyclohexane (30 μl, 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 4.5 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 column and a fraction obtained from the elution portion with hexane:ethyl acetate=3:1 was concentrated under reduced pressure, whereby the title compound (58 mg, 0.11 mmol, 59%) 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 hexane

Sources & evidence

ORD record
ord-928c9c1a46b1407bb8921bdad57f7c45
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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