4-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine → 4-Chloro-7-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 69318Notes

Reaction equation

HRID 69318 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][NH:10][C:6]=2[C:5]([O:11][CH3:12])=[CH:4][N:3]=1.ClC1C2C=NN([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)C=2C=CN=1>>[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)[C:6]=2[C:5]([O:11][CH3:12])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 867178134-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridineHCID 867178184-chloro-7-methoxy-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 867178194-Chloro-7-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Procedure

C5 was converted to the product using the method described for synthesis of 4-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine P3 in Preparation P3. The product was obtained as a light yellow oil, which solidified upon standing. Yield: 120 mg, 0.448 mmol, 41%. LCMS m/z 268.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.11-8.12 (m, 1H), 7.72 (s, 1H), 6.12 (dd, J=10.0, 2.6 Hz, 1H), 4.06 (s, 3H), 4.04-4.10 (m, 1H), 3.69-3.77 (m, 1H), 2.51-2.62 (m, 1H), 2.12-2.21 (m, 1H), 2.00-2.08 (m, 1H), 1.5-1.8 (m, 3H).

Workup

  1. customin Preparation P3
  2. customThe product was obtained as a light yellow oil, which

Sources & evidence

ORD record
ord-d9717efff24e45b4819ee02e8ed4d1bf
Source dataset
uspto-grants-2014_09
Patent number
US08822494B2

Reaction notes

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