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

HRID 748850노트

반응식

HRID 748850 반응식
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

참가 물질

8

반응물 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

생성물 1

HCID 231146576-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-N-cyclohexylmethylnicotinamide수율 59%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-928c9c1a46b1407bb8921bdad57f7c45
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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