Triethylamine → HCID 73336017, compound

HRID 710670Notes

Reaction equation

HRID 710670 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[C:4]2[CH2:14][CH2:13][CH2:12][C:5]=2[N:6]([CH2:8][C:9]([OH:11])=O)[N:7]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:48][C:49]1[CH:54]=[CH:53][C:52]([N:55]2[C:63]3[CH2:62][CH2:61][CH2:60][NH:59][C:58]=3[CH:57]=[N:56]2)=[CH:51][CH:50]=1>CN(C=O)C.O>[F:48][C:49]1[CH:50]=[CH:51][C:52]([N:55]2[C:63]3[CH2:62][CH2:61][CH2:60][N:59]([C:9](=[O:11])[CH2:8][N:6]4[C:5]5[CH2:12][CH2:13][CH2:14][C:4]=5[C:3]([C:2]([F:1])([F:16])[F:15])=[N:7]4)[C:58]=3[CH:57]=[N:56]2)=[CH:53][CH:54]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 653577333309-24-3HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 73336017HCID 73336017, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution 2-[3-(trifluoromethyl)-5,6-dihydro-4H-cyclopenta[c]pyrazol-1-yl]acetic acid (83 mg, 0.35 mmol) in DMF (2 mL) was added Et3N (75 μL, 0.525 mmol), HATU (160 mg, 0.42 mmol), followed by 1-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (77 mg, 0.35 mmol) at room temperature. The resulting solution was then stirred at 50° C. for 30 min. The reaction mixture was then cooled to room temperature, H2O (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined EtOAc layers were dried (MgSO4), filtered, and concentrated in vacuo. Purification by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the desired product as a white powder (0.011 g, 0.025 mmol, 7%). 1H NMR (400 MHz, DMSO-d6) δ 8.15 (s, 1H), 7.6 (m, 2H), 7.35 (t, 2H, J=8.6, 17.6 Hz), 5.38 (s, 2H), 3.77 (m, 2H), 2.85 (t, 2H, J=6.3, 12.5 Hz), 2.66 (m, 4H), 2.53 (m, 2H), 1.97 (m, 2H); MS: (ES) m/z calculated for C21H19F4N5O [M+H]+ 434.2, found 434.1.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionthe mixture was extracted with EtOAc (2×20 mL)
  3. dry with materialThe combined EtOAc layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-05bd1a9fe94d4b4b86522bf2bd4ba1e3
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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