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Triethylamine → HCID 59834743, 화합물

HRID 271578
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HRID 271578 반응식
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.[N:25]1([CH2:30][CH2:31][CH2:32][NH2:33])[CH:29]=[CH:28][N:27]=[CH:26]1.C(N(CC)CC)C.[O-]S([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO.CC(C)=O>[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:33][CH2:32][CH2:31][CH2:30][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH2:18][CH2:17]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 787361H-Imidazole-1-propanamineHCID 4311764Sodium borohydrideHCID 9880368HCID 9880368, 화합물

생성물 1

HCID 59834743HCID 59834743, 화합물수율 73%

시약·촉매·용매 3

HCID 180Acetone용매
HCID 887Methanol용매
HCID 6344Dichloromethane용매

실험 절차

To the mixture of 100 mg (0.30 mmoles) of 7-(2,2-dimethyl-propyl)-6-(4-oxo-piperidin-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile, 60 mg (0.48 mmoles) of 3-Imidazol-1-yl-propylamine and 0.15 ml (1.1 mmoles) of triethylamine in 5 ml of CH2Cl2, 58 mg (1.1 mmoles) of MgSO4 is added at ambient temperature. The mixture is stirred for 15.5 hours at ambient temperature. The reaction mixture is filterlated to remove MgSO4 and concentrated under reduced pressure to give crude imine. To a solution of crude imine in 5 ml of MeOH, 13 mg (0.33 mmoles) of NaBH4 is added at −10-−20° C., and the reaction mixture is stirred at 0° C. for 4.5 hours. After addition of 5 ml of acetone, the mixture is concentrated, diluted with H2O, and then extracted with CH2Cl2. The combined extrats are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 95 mg of desired 7-(2,2-dimethyl-propyl)-6-[4-(3-imidazol-1-yl-propylamino)-piperidin-1-ylmethyl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 73% yield.

후처리

  1. additionis added at ambient temperature
  2. customto remove MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customto give crude imine
  5. stirringthe reaction mixture is stirred at 0° C. for 4.5 hours
  6. concentrationthe mixture is concentrated
  7. additiondiluted with H2O
  8. extractionextracted with CH2Cl2
  9. washThe combined extrats are washed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2abdab5832ff42f3a473b11f0f481540
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452886B2

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