Aluminium lithium hydride → HCID 90416186, compound

HRID 1050032Notes

Reaction equation

HRID 1050032 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[N:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([CH2:37][C:38]([CH3:45])([CH3:44])[C:39](OCC)=[O:40])=[C:33]([C:46]([F:49])([F:48])[F:47])[CH:32]=3)=[O:29])=[C:23]([F:50])[CH:22]=2)=[C:17]([O:51][CH2:52][CH3:53])[CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:14][C:15]1[N:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([CH2:37][C:38]([CH3:45])([CH3:44])[CH2:39][OH:40])=[C:33]([C:46]([F:47])([F:49])[F:48])[CH:32]=3)=[O:29])=[C:23]([F:50])[CH:22]=2)=[C:17]([O:51][CH2:52][CH3:53])[CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90416102HCID 90416102, compound

Product 1

HCID 90416186HCID 90416186, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

LAH (17.45 mg, 0.460 mmol) was added to a solution of ethyl 3-(4-(2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-2-fluorophenyl)acetamido)-2-(trifluoromethyl)phenyl)-2,2-dimethylpropanoate (100 mg, 0.153 mmol) in THF (5 mL). The reaction mixture was stirred at 25° C. for 1 h. The reaction was then extracted with EA (50 mL), washed with water and NaOH solution and dried over Na2SO4. The combined organic extracts were purified by preparative TLC (PE/EA=2:1, Rf=0.4) to yield a light yellow oil of 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-2-fluorophenyl)-N-(4-(3-hydroxy-2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl)acetamide (20 mg, 0.032 mmol, 20.9% yield): 1H NMR (400 MHz, CD3OD) δ 7.94-8.03 (m, 2H) 7.77 (d, J=8.53 Hz, 1H) 7.46 (t, J=7.53 Hz, 3H) 7.36-7.43 (m, 3H) 7.27-7.35 (m, 3H) 6.52 (s, 1H) 5.38 (s, 2H) 3.83 (s, 2H) 2.81 (s, 2H) 2.03 (s, 4H) 1.40 (t, J=6.78 Hz, 3H) 1.26 (t, J=7.28 Hz, 3H) 0.82-0.90 (m, 6H); ES-LCMS m/z 611 (M+H).

Workup

  1. extractionThe reaction was then extracted with EA (50 mL)
  2. washwashed with water and NaOH solution
  3. dry with materialdried over Na2SO4
  4. customThe combined organic extracts were purified by preparative TLC (PE/EA=2:1, Rf=0.4)

Sources & evidence

ORD record
ord-b89578ced967431aa02ad587fa0a6f6a
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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