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

HRID 1246725노트

반응식

HRID 1246725 반응식
[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

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1fa1253543254d1f9473d75cf2d81740
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129235B2

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