2-(4-Fluorophenyl)-3-(2-fluoro-4-pyridinyl)-pyrazolo[1,5-a]pyridine → 4-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[2-(1H-imidazol-5-yl)ethyl]-2-pyridinamine

HRID 1374707Notes

Reaction equation

HRID 1374707 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](F)[CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[NH2:24][CH2:25][CH2:26][C:27]1[N:31]=[CH:30][NH:29][CH:28]=1>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:24][CH2:25][CH2:26][C:27]4[NH:31][CH:30]=[N:29][CH:28]=4)[CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 99443962-(4-Fluorophenyl)-3-(2-fluoro-4-pyridinyl)-pyrazolo[1,5-a]pyridineHCID 178419017HCID 178419017, compound

Product 1

HCID 101114674-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[2-(1H-imidazol-5-yl)ethyl]-2-pyridinamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

In a sealed-tube was combined 2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridine (Example 27. 30 mg, 0.10 mmol) and histamine (40 mg, 0.36 mmol), and the reaction was placed in a pre-heated oil bath at 140° C. The reaction was stirred at 140° C. until consumption of starting material was indicated by TLC analysis (50% ethyl acetate in hexanes). The contents of the sealed-tube were transferred to a flask and concentrated to dryness at 50° C. under high vacuum. The residue was purified by silica gel chromatography to yield the title compound, 23 mg (0.06 mmol, 60%). 1H NMR (d6-DMSO) δ 11.8 (brs, 1H), 8.73 (d, 1H, J=6.8 Hz), 7.94 (d, 1H, J=5.3 Hz), 7.63 (d, 1H, J=9.3 Hz), 7.57 (dd, 2H, J=5.3, 8.6 Hz), 7.48 (s, 1H), 7.30 (t, 1H, J=7.6 Hz), 7.23 (t, 2H, J=9.0 Hz), 6.97 (t, 1H, J=6.8 Hz), 6.75 (brs, 1H), 6.57 (br t, 1H, J=5.3 Hz), 6.44 (s, 1H), 6.33 (d, 1H, J=5.3 Hz), 3.41 (q, 2H, J=6.6 Hz), 2.7 (t, 2H, J=6.6 Hz). MS (ES+ve): 399.1 (50, M+), 305.3 (90), 169.4 (100).

Workup

  1. customIn a sealed-tube was combined
  2. customThe contents of the sealed-tube were transferred to a flask
  3. concentrationconcentrated to dryness at 50° C. under high vacuum
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b6776ded3b5c4e09b5924989adec4176
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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