Lithium Hydroxide → HCID 57899090, compound

HRID 1404239Notes

Reaction equation

HRID 1404239 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 1M 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) ppm 0.95-1.04 (m, 2 H) 1.44 (dd, J=12.51, 2.91Hz, 2 H) 1.67 (br. s., 1 H) 1.74-1.87 (m, 6 H) 2.47 (m, 1 H) 2.60 (s, 3 H) 7.25 (d, J=8.59 Hz, 1 H) 7.30 (d, J=8.34 Hz, 2 H) 7.56 (d, J=8.34 Hz, 2 H) 7.66 (d, J=8.34 Hz, 1 H) 7.97 (dd, J=8.72, 2.65 Hz, 1 H) 8.48 (d, J=2.27 Hz, 1 H) 8.67 (d, J=8.34 Hz, 1 H) 8.80 (s, 1 H); 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-de23ee92dc18441a9c50816dd53c6325
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

Loading…