HCID 86635863, compound → HCID 86635862, compound

HRID 2098511Notes

Reaction equation

HRID 2098511 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][C:17]2([OH:21])[CH2:20][CH2:19][CH2:18]2)[CH:10]=1)=[O:4]>CCO>[F:1][C:2]([F:22])([F:23])[C:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][C:17]2([OH:21])[CH2:18][CH2:19][CH2:20]2)[CH:10]=1)=[O:4]

Participants

3

Reactant 1

HCID 86635863HCID 86635863, compound

Product 1

HCID 86635862HCID 86635862, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,2,2-Trifluoro-N-(2-(3-(2-(1-hydroxy cyclobutyl)ethynyl)phenoxy)ethyl)acetamide (0.45 g, 1.9 mmol) in EtOH (20 mL) was degassed and purged with nitrogen. To this was added Pd on C (0.09 g, 10%) and the flask was evacuated and filled with hydrogen. The resulting reaction mixture was stirred at room temperature under hydrogen balloon overnight. This was followed by filteration through a pad of Celite. The filter cake was washed with ethanol and the filtrate concentrated to afford 2,2,2-trifluoro-N-(2-(3-(2-(1-hydroxycyclobutyl)ethyl)phenoxy)ethyl)acetamide as yellow oil. Yield (0.3 g, 66%): 1H NMR (400 MHz, DMSO-d6) δ 7.20-7.25 (m, 1H), 6.87 (d, J=7.6 Hz, 1H), 6.78 (s, 1H), 6.72 (dd, J=8.0, 2.4 Hz, 1H), 4.11 (t, J=5.0 Hz, 2H), 3.76-3.81 (m, 2H), 2.67-2.72 (m, 2H), 2.01-2.14 (m, 4H), 1.92-1.96 (m, 2H), 1.22-1.26 (m, 2H).

Workup

  1. custompurged with nitrogen
  2. additionTo this was added Pd on C (0.09 g, 10%)
  3. customthe flask was evacuated
  4. additionfilled with hydrogen
  5. customThe resulting reaction mixture
  6. washThe filter cake was washed with ethanol
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-2d39e912ec5142f38070476cd0beb264
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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