Pyridine → N-(4-chlorophenyl)-1-pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 1246725ノート

反応式

HRID 1246725 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH:11]=[C:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1.C(Cl)(C(Cl)=O)=O.N1C=CC=CC=1.[Cl:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1>C(Cl)Cl.C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.O.CN(C=O)C>[Cl:28][C:29]1[CH:35]=[CH:34][C:32]([NH:33][C:13]([C:10]2[CH2:9][CH2:8][N:7]([C:2]3[N:1]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:12][CH:11]=2)=[O:15])=[CH:31][CH:30]=1

参加物

10

反応物 4

HCID 1049PyridineHCID 78124-ChloroanilineHCID 65578Oxalyl chlorideHCID 219047301-Pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxylic acid

生成物 1

HCID 11324497N-(4-chlorophenyl)-1-pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxamide

試薬・触媒・溶媒 5

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

1-Pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxylic acid (55.0 mg, 0.27 mmol) and a catalytic amount of DMF were combined in CH2Cl2 (1.5 mL) and treated with (COCl)2 (0.033 mL, 0.38 mmol). The mixture was stirred for 90 minutes, diluted with toluene (0.5 mL), and concentrated to dryness under reduced pressure. The residue in CH2Cl2 (1.5 mL) was treated with pyridine (0.033 mL, 0.41 mmol), catalytic amount of DMAP, and 4-chloroaniline (41.0 mg, 0.32 mmol). The mixture was stirred for 1 hour, diluted with water, and extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residure was purified by flash chromatography (15% ethyl acetate/CH2Cl2) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.35 (d, 2H), 7.51 (d, 2H), 7.39 (brs, 1H), 7.31 (d, 2H), 6.77 (sept, 1H), 6.54 (t, 1H), 4.43 (q, 2H), 4.03 (t, 2H), 2.58 (m, 2H); MS (m/z) 315.

後処理

  1. concentrationconcentrated to dryness under reduced pressure
  2. stirringThe mixture was stirred for 1 hour
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residure was purified by flash chromatography (15% ethyl acetate/CH2Cl2)

出典と根拠

ORDレコード
ord-1fa1253543254d1f9473d75cf2d81740
出典データセット
uspto-grants-2006_10
特許番号
US07129235B2

反応ノート

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