1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 73335638, compound

HRID 710638Notes

Reaction equation

HRID 710638 reaction equation
[OH:1][C:2]([C:5]1[CH:9]=[C:8]([CH3:10])[N:7]([CH:11]([CH2:15][CH3:16])[C:12]([OH:14])=O)[N:6]=1)([CH3:4])[CH3:3].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH2:29][NH:28][C:27]=3[CH:26]=[N:25]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH2:29][N:28]([C:12](=[O:14])[CH:11]([N:7]4[C:8]([CH3:10])=[CH:9][C:5]([C:2]([OH:1])([CH3:3])[CH3:4])=[N:6]4)[CH2:15][CH3:16])[C:27]=3[CH:26]=[N:25]2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 86711676HCID 86711676, compound

Product 1

HCID 73335638HCID 73335638, compound

Procedure

The title compound was prepared from 2-(3-(2-hydroxypropan-2-yl)-5-methyl-1H-pyrazol-1-yl)butanoic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method A. The reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide 3.7 mg of the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.46 (s, 1H), 7.44 (m, 2H), 7.15 (t, J=8.6 Hz, 2H), 5.92 (s, 1H), 5.17 (dd, J=7.4, 7.4 Hz, 1H), 3.73 (m, 1H), 3.48 (m, 1H), 2.75 (m, 2H), 2.33 (m, 1H), 2.23 (s, 3H), 2.17 (s, 1H), 2.14 (m, 1H), 1.87 (m, 1H), 1.73 (m, 1H), 1.52 (s, 6H), 0.96 (t, J=7.4 Hz, 3H); MS: (ES) m/z calculated for C23H29FN5O2 [M+H]+ 426.2, found 426.2.

Workup

  1. customThe reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-e09071000a0d4dda86d03e2af16d3b3c
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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