Triethylamine → HCID 73336115, compound

HRID 710673Notes

Reaction equation

HRID 710673 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=O)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[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:1]4[C:5]5=[N:6][CH:7]=[CH:8][CH:9]=[C:4]5[CH:3]=[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 22139374(1H-Pyrrolo[2,3-b]pyridin-1-yl)acetic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 73336115HCID 73336115, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-pyrrolo[2,3-b]pyridin-1-ylacetic acid (51.2 mg, 0.24 mmol), 1-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (50.3 mg, 0.29 mmol), triethyl amine (200 μL, 1.4 mmol), and HATU (110.7 mg, 0.29 mmol) in DMF (1 mL) was stirred at room temperature for 2 hours. The reaction mixture was then 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, 70% ethyl acetate in hexanes) to afford the desired product (25.9 mg, 0.07 mmol, 28%). 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 0.8H), 8.30 (dd, J=4.8, 1.6 Hz, 1H), 7.94 (dd, J=7.2, 1.6 Hz, 1H), 7.81 (s, 0.2H), 7.45 (m, 2H), 7.36 (d, J=3.6 Hz, 0.8H), 7.31 (d, J=3.6 Hz, 0.2H), 7.18 (m, 2H), 7.09 (dd, J=7.6, 4.8 Hz, 1H), 6.58 (d, J=3.6 Hz, 1H), 5.44 (s, 0.2H), 5.32 (s, 0.8H), 3.91 (m, 2H), 2.84 (m, 2H), 2.07 (m, 2H); MS: (ES) m/z calculated for C21H18FN5O [M+H]+ 376.1, found 376.1.

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, 70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-104a3440b07a49b084a78e17ee1fe992
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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