Diisopropylcarbodiimide → 4-(4-Iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid (3,5-dichloro-phenyl)-amide

HRID 2180192ノート

反応式

HRID 2180192 の反応式
N1C=CC=CC=1.[I:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:21]([OH:23])=O)[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[Cl:24][C:25]1[CH:26]=[C:27]([NH:32]C2C=CC=CC=2)[CH:28]=[C:29]([Cl:31])[CH:30]=1.CC(C)N=C=NC(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:24][C:25]1[CH:26]=[C:27]([NH:32][C:21]([C:14]2([C:11]3[CH:10]=[CH:9][C:8]([I:7])=[CH:13][CH:12]=3)[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)=[O:23])[CH:28]=[C:29]([Cl:31])[CH:30]=1

参加物

6

反応物 3

HCID 12734DiisopropylcarbodiimideHCID 190041313,5-Dichloro-N-phenylanilineHCID 685340374-(4-Iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid pyridine salt

生成物 1

HCID 865871764-(4-Iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid (3,5-dichloro-phenyl)-amide収率 34.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(4-iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid pyridine salt (440 mg, 1.04 mmol, see Example 6) and 3,5-dichlorophenylaniline (0.20 g, 1.24 mmol, 1.2 eq.) in anhydrous DMF (5 mL) was added DIC (0.326 mL, 2.08 mmol, 2 eq.) followed by DMAP (0.006 g, 0.052 mmol, 5 mol %). The mixture was stirred at room temperature for 16 h and then it was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was separated, washed with H2O (3×40 mL) and saturated brine (50 mL), dried over Na2SO4, filtered and concentrated by rotary evaporation. The crude material was purified by silica gel chromatography by eluting with 10% MeOH/EtOAc to give 175 mg (34%) of 4-(4-iodo-phenyl)-1-methyl-piperidine-4-carboxylic acid (3,5-dichloro-phenyl)-amide as a white solid. MS(ESI): 489.1/491.1.

後処理

  1. customit was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL)
  2. customThe organic layer was separated
  3. washwashed with H2O (3×40 mL) and saturated brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customThe crude material was purified by silica gel chromatography
  8. washby eluting with 10% MeOH/EtOAc

出典と根拠

ORDレコード
ord-2e6b5e932e70485487d7575f37d06da7
出典データセット
uspto-grants-2005_05
特許番号
US06887889B2

反応ノート

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