1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 73335439, compound

HRID 710630Notes

Reaction equation

HRID 710630 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([F:17])([F:16])[F:15])=[N:4][N:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)[C:6]=1[CH3:7].[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:33]3[CH2:32][CH2:31][CH2:30][NH:29][C:28]=3[CH:27]=[N:26]2)=[CH:21][CH:20]=1>>[Cl:1][C:2]1[C:3]([C:14]([F:17])([F:16])[F:15])=[N:4][N:5]([C:8]([CH3:13])([CH3:12])[C:9]([N:29]2[CH2:30][CH2:31][CH2:32][C:33]3[N:25]([C:22]4[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=4)[N:26]=[CH:27][C:28]2=3)=[O:11])[C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 86711672HCID 86711672, compound

Product 1

HCID 73335439HCID 73335439, compoundYield 68%

Procedure

The title compound was from prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-2-methylpropanoic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 2×1 M NaHSO4. The organic layer was concentrated and the residue was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes) to provide 80 mg (68%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.44 (m, 2H), 7.16 (m, 2H), 3.08 (m, 2H), 2.74 (t, J=6.6 Hz, 2H), 2.21 (s, 3H), 1.91 (s, 6H), 1.76 (ddd, J=5.8, 6.2, 10.5 Hz, 2H); MS: (ES) m/z calculated for C21H21ClF4N5O [M+H]+ 470.1, found 470.1.

Workup

  1. washThe product mixture was washed with 2×1 M NaHSO4
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d885ccb0956045b7a56f89bcc102faf9
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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