Sodium Hydroxide → HCID 58966530, compound

HRID 390752Notes

Reaction equation

HRID 390752 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[CH:25]([N:28]1[CH2:33][CH2:32][C:31]([F:38])([C:34]([O:36]C)=[O:35])[CH2:30][CH2:29]1)[CH2:26][CH3:27])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[OH-].[Na+]>CO.O>[F:44][C:42]([F:43])([F:45])[C:40]1[CH:39]=[C:5]([CH:4]=[C:3]([C:2]([F:47])([F:46])[F:1])[CH:41]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:16]=1[CH:25]([N:28]1[CH2:33][CH2:32][C:31]([F:38])([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]1)[CH2:26][CH3:27])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58966462HCID 58966462, compound

Product 1

HCID 58966530HCID 58966530, compoundYield 406.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 1-{1-[2-({[3,5-bis(trifluoromethyl)benzyl](2-methyl-2H-tetrazol-5-yl)amino}methyl]-4-(trifluoromethyl)phenyl]propyl}-4-fluoropiperidine-4-carboxylate (example 204) (0.23 g, 0.33 mMol) in methanol was added 1N sodium hydroxide (1.8 mL.) and the solution was microwaved for 30 minutes at 100° C. The reaction mixture was diluted with water and the pH was adjusted to 3 and was extracted with dichloromethane. The organic extract was dried, concentrated and purified by flash chromatography to afford the title compound (0.9 g., 40%), 1HNMR (400 MHz. CDCl3) δ 7.90 (t, 1H), 7.80 (s, 1H), 7.60 (m, 37.15 (m, 1H), 4.70 (dd, 4H), 4.6 (m, 2H), 4.40 m, 2H), 4.10 (s, 3H), 3.80 (m, 1H), 2.90 (m, 1H), 3.60 (m, 2H), 2.40(m, 2H), 2.15 (m, 1H), 2.10 (m, 2H), 1.9 (m, 1H), 0.5 (t, 3H). MS (ES+) Calc 670.55, Found 671.4 (M+1)

Workup

  1. customthe solution was microwaved for 30 minutes at 100° C
  2. extractionwas extracted with dichloromethane
  3. extractionThe organic extract
  4. customwas dried
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-49df5e3a8d404134881d5a3b29d9f95d
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Reaction notes

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