Diisopropylethylamine → HCID 73335128, compound

HRID 710640Notes

Reaction equation

HRID 710640 reaction equation
[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

Participants

8

Reactant 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 17024870HCID 17024870, compoundHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 73335128HCID 73335128, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-6b86b6c5a5d4432c891fb9ff44f99c49
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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