Diisopropylethylamine → 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-pyridazin-3-yl-propionamide

HRID 398503

반응식

HRID 398503 반응식
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:52][C:53]1[N:54]=[N:55][CH:56]=[CH:57][CH:58]=1>CN(C)C=O>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH:52][C:53]2[N:54]=[N:55][CH:56]=[CH:57][CH:58]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 230373AminopyridazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27627253-cyclopentyl-2-(3,4-dichlorophenyl)propanoic Acid

생성물 1

HCID 99289973-cyclopentyl-2-(3,4-dichlorophenyl)-N-pyridazin-3-yl-propionamide수율 62.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-cyclopentyl-2-(3,4-dichlorophenyl)-propionic acid (prepared as in Example 38A, 625.2 mg, 2.18 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (908.3 mg, 2.39 mmol), N,N-diisopropylethylamine (1.1 mL, 6.53 mmol), and 3-aminopyridazine (310.6 mg, 3.27 mmol) in dry N,N-dimethylformamide (11 mL) was stirred at 25° C. under nitrogen for 72 h. The reaction mixture was concentrated in vacuo to remove N,N-dimethylformamide. The resulting residue was diluted with ethyl acetate (200 mL). The organic layer was washed with a 10% aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-pyridazin-3-yl-propionamide (493.8 mg, 62%) as a white foam: mp 70-71° C.; EI-HRMS m/e calcd for C18H19Cl2N3O (M+) 363.0905, found 363.0908.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove N,N-dimethylformamide
  3. additionThe resulting residue was diluted with ethyl acetate (200 mL)
  4. washThe organic layer was washed with a 10% aqueous hydrochloric acid solution
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d4a333aacee24d63a7fd44bedc23c4ad
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610846B1

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