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

HRID 748850ノート

反応式

HRID 748850 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-928c9c1a46b1407bb8921bdad57f7c45
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

反応ノート

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