Sodium Hydroxide → HCID 9868762, compound

HRID 1816013Notes

Reaction equation

HRID 1816013 reaction equation
[OH-].[Na+].[CH3:3][NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)[CH2:22][C:23]([O:25]CC)=[O:24])=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=1>CO>[CH3:3][NH:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH:21]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:33]=3)[CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:19]=2)[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20775658HCID 20775658, compound

Product 1

HCID 9868762HCID 9868762, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 N NaOH (8.2 mL, 0.823 mmole) was added dropwise to a cooled (15° C.) solution of ethyl (±)-4-[4-[2-[6-(methylamino)pyridin-2-yl]-1 ethoxy]phenyl]-3-[4-(trifluoromethyl)phenyl)butanoate (200 mg, 0.41 mmole) in MeOH (3 mL), and the mixture was stirred at RT for 24 hr. The resulting solution was concentrated in vacuum and the residue was dissolved in H2O (5 mL). The pH was adjusted to 5 with 1.0 N HCl, and the precipitate was collected, washed with small amount of water, and dried in vacuum at 60° C. The title compound (120 mg, 64%) was obtained as a white, foamy solid: MS (ES) me 459 (M+H)+. Anal. Calcd for C25H25FN2O3.0.85H2O: C, 63.38; H, 5.68; N, 5.91. Found: C, 63.23; H, 5.41; N, 5.73.

Workup

  1. concentrationThe resulting solution was concentrated in vacuum
  2. dissolutionthe residue was dissolved in H2O (5 mL)
  3. customthe precipitate was collected
  4. washwashed with small amount of water
  5. customdried in vacuum at 60° C

Sources & evidence

ORD record
ord-c2b8963d94b14801a48349096385026c
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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