4-Methylmorpholine → 5-Tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide

HRID 2243188

반응식

HRID 2243188 반응식
[OH-].[K+].CO[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][N:8]=1)=[O:6].[Cl:17][C:18]1[CH:19]=[C:20]([CH2:25][CH2:26][NH2:27])[CH:21]=[CH:22][C:23]=1[Cl:24].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH2:25][CH2:26][NH:27][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][N:8]=2)=[O:6])[CH:21]=[CH:22][C:23]=1[Cl:24]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 14797Potassium HydroxideHCID 2179583,4-DichlorophenethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10774153HCID 10774153, 화합물

생성물 1

HCID 670177025-Tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide수율 58.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Potassium hydroxide (2 M aq. solution, 0.98 mL, 1.96 mmol) was added at RT to a solution of 5-tert-butyl-pyridine-2-carboxylic acid methyl ester (synthesized according to J. Org. Chem. 1998, 63, 7840-7850; 189 mg, 0.98 mmol) in THF (2.6 mL), then after stirring for 2 h, the reaction mixture was evaporated. The residue was taken up in DMF (12 mL), then after addition of 2-(3,4-dichloro-phenyl)-ethylamine (204 mg, 1.07 mmol), 4-methylmorpholine (297 mg, 2.93 mmol), and HBTU (556 mg, 1.47 mmol), the reaction mixture was stirred at RT for 16 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and concentrated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced 5-tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide (200 mg, 58%). White solid, MS (ISP): 351.4 (M+H)+.

후처리

  1. customthe reaction mixture was evaporated
  2. stirringthe reaction mixture was stirred at RT for 16 h
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-457ea0d6351e45cea2190369d974942f
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674815B2

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