Diisopropylethylamine → HCID 73335128、化合物

HRID 710640ノート

反応式

HRID 710640 の反応式
[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

参加物

8

反応物 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

生成物 1

HCID 73335128HCID 73335128、化合物収率 89%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6b86b6c5a5d4432c891fb9ff44f99c49
出典データセット
uspto-grants-2015_11
特許番号
US09181241B2

反応ノート

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