Diisopropylethylamine → HCID 73335128, 화합물

HRID 710640노트

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HRID 710640 반응식
[CH3:1][C:2]1[N:6]([CH:7]([CH3:11])[C:8]([OH:10])=O)[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[F:49][C:50]1[CH:55]=[CH:54][C:53]([N:56]2[C:64]3[CH2:63][CH2:62][CH2:61][NH:60][C:59]=3[CH:58]=[N:57]2)=[CH:52][CH:51]=1>O.C(OCC)(=O)C.CN(C)C=O>[F:49][C:50]1[CH:51]=[CH:52][C:53]([N:56]2[C:64]3[CH2:63][CH2:62][CH2:61][N:60]([C:8](=[O:10])[CH:7]([N:6]4[C:2]([CH3:1])=[CH:3][C:4]([C:12]([F:15])([F:14])[F:13])=[N:5]4)[CH3:11])[C:59]=3[CH:58]=[N:57]2)=[CH:54][CH:55]=1

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 170248702-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]propanoic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

생성물 1

HCID 73335128HCID 73335128, 화합물수율 89%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Dimethylformamide (1 mL) was added to a mixture containing 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]propanoic acid (49.6 mg, 0.223 mmol) and HATU (89.1 mg, 0.234 mmol). Diisopropylethylamine (98 μL, 0.56 mmol) was added at room temperature and the reaction mixture was stirred for 1 minute. 1-(4-Fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (49.5 mg, 0.228 mmol) was added all at once and the reaction mixture was stirred at room temperature overnight. Ethyl acetate and water were then added and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 20-38% ethyl acetate in hexanes) to afford the desired product as a white solid (83.5 mg, 0.198 mmol, 89%). 1H NMR (400 MHz, CDCl3) δ 8.45 (s, 1H), 7.44 (ddd, J=9.2, 5.2, 2.0 Hz, 2H), 7.15 (dt, J=8.8, 2.0 Hz, 2H), 6.31 (s, 1H), 5.55 (q, J=7.2 Hz, 1H), 3.73 (ddd, J=13, 7.6, 3.2 Hz, 1H), 3.37 (ddd, J=12, 8.8, 3.2 Hz, 1H), 2.72-2.79 (m, 2H), 2.29 (s, 3H), 1.86-1.97 (m, 1H), 1.76-1.85 (m, 1H), 1.80 (d, J=7.2 Hz, 3H); MS: (ES) m/z calculated for C20H19N5OF4 [M+H]+ 422, found 422.

후처리

  1. stirringwas stirred at room temperature overnight
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted twice more with ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (SiO2, 20-38% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-6b86b6c5a5d4432c891fb9ff44f99c49
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181241B2

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