Triethylamine → HCID 73336018, compound

HRID 710674Notes

Reaction equation

HRID 710674 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:10][C:11]([OH:13])=O)[CH:2]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:29]3[CH2:28][CH2:27][CH2:26][NH:25][C:24]=3[CH:23]=[N:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(=O)(O)[O-].[Na+]>[F:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[C:29]3[CH2:28][CH2:27][CH2:26][N:25]([C:11](=[O:13])[CH2:10][N:3]4[C:4]5=[N:5][CH:6]=[CH:7][CH:8]=[C:9]5[N:1]=[CH:2]4)[C:24]=3[CH:23]=[N:22]2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57283456HCID 57283456, compoundHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 73336018HCID 73336018, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-imidazo[4,5-b]pyridin-3-ylacetic acid (251.7 mg, excess), 1-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (42.7 mg, 0.23 mmol), triethyl amine (200 μL, 1.4 mmol), and HATU (87.9 mg, 0.23 mmol) in DMF (1 mL) was stirred at room temperature for 2 hours. The reaction mixture was diluted with 10 mL of aqueous saturated sodium bicarbonate, and extracted with EtOAc (2×15 mL). The combined organic layers were then washed with water (2×20 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 10% MeOH in EtOAc) to afford the desired product (26.1 mg, 0.07 mmol, 30%). 1H NMR (400 MHz, CDCl3) δ 8.38 (d, J=7.2 Hz 1H), 8.50 (s, 0.8H), 8.25 (s, 0.2H), 8.12 (d, J=5.6 Hz, 1H), 7.45 (m, 2H), 7.28 (m, 1H), 7.15 (m, 2H), 5.46 (s, 0.2H), 5.33 (s, 0.8H), 3.95 (m, 2H), 2.88 (m, 2H), 2.15 (m, 2H); MS: (ES) m/z calculated for C20H17FN6O [M+H]+ 377.1, found 377.1.

Workup

  1. extractionextracted with EtOAc (2×15 mL)
  2. washThe combined organic layers were then washed with water (2×20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (SiO2, 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-e06423b3c591422eb7381610c7bd6b6f
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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