Lithium Hydroxide → HCID 57899090, compound

HRID 76047Notes

Reaction equation

HRID 76047 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[N:19][C:20]([NH:23][C:24]4[C:25]([CH3:34])=[N:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=4)=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[Li+].[OH-]>C1COCC1.CO>[CH3:34][C:25]1[C:24]([NH:23][C:20]2[N:19]=[CH:18][C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH:8]4[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:35])=[O:2])[CH2:6][CH2:7]4)=[CH:12][CH:13]=3)=[CH:22][CH:21]=2)=[CH:29][CH:28]=[C:27]([C:30]([F:32])([F:31])[F:33])[N:26]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66615758(4-{4-[6-(2-Methyl-6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 57899090HCID 57899090, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(4-{4-[6-(2-Methyl-6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester (332 g, 0.69 mmol) was dissolved in THF/MeOH (3:1, 4 mL) and to it was added aqueous LiOH (4M, 1 mL). The mixture was stirred at room temperature for 18 hours, then the organic solvent was removed via rotary evaporation. The remaining crude was diluted with water and the pH was adjusted to 2 with 1 M HCl. The resulting precipitate was collected by filtration and dried under vacuum to obtain the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.04 (m, 2H) 1.44 (dd, J=12.51, 2.91 Hz, 2H) 1.67 (br. s., 1H) 1.74-1.87 (m, 6H) 2.47 (m, 1H) 2.60 (s, 3H) 7.25 (d, J=8.59 Hz, 1H) 7.30 (d, J=8.34 Hz, 2H) 7.56 (d, J=8.34 Hz, 2H) 7.66 (d, J=8.34 Hz, 1H) 7.97 (dd, J=8.72, 2.65 Hz, 1H) 8.48 (d, J=2.27 Hz, 1H) 8.67 (d, J=8.34 Hz, 1H) 8.80 (s, 1H); MS (M+H)+470.3.

Workup

  1. customthe organic solvent was removed via rotary evaporation
  2. additionThe remaining crude was diluted with water
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d977f880486c4c4a9fc0f2c1c1ad00a0
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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