Potassium Carbonate → HCID 68379922, 화합물

HRID 2178649노트

반응식

HRID 2178649 반응식
C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:8][C:9]1[N:10]=[CH:11][N:12]([C:14]2[C:19](=[O:20])[NH:18][C:17]([C:21]([OH:23])=O)=[CH:16][CH:15]=2)[CH:13]=1.Cl.[Cl:25][CH2:26][CH2:27][NH:28][CH2:29][CH2:30]Cl.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[Cl:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][N:18]2[C:19](=[O:20])[C:14]([N:12]3[CH:13]=[C:9]([CH3:8])[N:10]=[CH:11]3)=[CH:15][CH:16]=[C:17]2[C:21]1=[O:23]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68380187HCID 68380187, 화합물

생성물 1

HCID 68379922HCID 68379922, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Potassium carbonate (195.4 g, 1414 mmol) was added to a mixture of 5-(4-methyl-1H-imidazol-1-yl)-6-oxo-1,6-dihydropyridine-2-carboxylic acid, hydrochloride salt (C3) (34.5 g, 135 mmol) and 2-chloro-N-(2-chloroethyl)ethanamine hydrochloride (37.8 g, 212 mmol) in N,N-dimethylformamide (670 mL), and the reaction was stirred for 10 minutes. O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 83.5 g, 219 mmol) was added and stirring was continued for an additional 3 hours and 40 minutes. The reaction mixture was then poured into water (4 L) and stirred for 30 minutes. After extraction with dichloromethane (3×1 L), the combined organic layers were washed with saturated aqueous sodium chloride solution (3×3 L), dried over magnesium sulfate, filtered and concentrated in vacuo. Finally, most of the DMF was removed by using a methanol/liquid nitrogen cooler. The residue was stirred in ethyl acetate (approximately 50 mL) for 30 minutes. The solids were collected by filtration and washed with ethyl acetate and pentane, providing the title compound as a yellow solid. Yield: 23.0 g, 75.0 mmol, 56%. LCMS m/z 307.1 (M+1). 1H-NMR (300 MHz, CDCl3) δ 2.29 (br s, 3H), 3.80-3.93 (m, 6H), 4.38-4.44 (m, 2H), 7.13-7.16 (m, 1H), 7.27 (d, J=7.6 Hz, 1H), 7.45 (d, J=7.6 Hz, 1H), 8.24 (d, J=1.0 Hz, 1H).

후처리

  1. stirringstirring
  2. waitwas continued for an additional 3 hours and 40 minutes
  3. stirringstirred for 30 minutes
  4. extractionAfter extraction with dichloromethane (3×1 L)
  5. washthe combined organic layers were washed with saturated aqueous sodium chloride solution (3×3 L)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customFinally, most of the DMF was removed
  10. stirringThe residue was stirred in ethyl acetate (approximately 50 mL) for 30 minutes
  11. filtrationThe solids were collected by filtration
  12. washwashed with ethyl acetate and pentane

출처 및 근거

ORD 기록
ord-c687af600a6d4d3fa4be92ccdc629d8d
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067934B2

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