Potassium Carbonate → HCID 66932107, compound

HRID 1958829Notes

Reaction equation

HRID 1958829 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8]Br)(=O)C.[CH2:10]([C:12]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH2:30][N:31]([CH2:33][CH3:34])[CH3:32])[CH:24]=3)[O:20][N:19]=2)[CH:15]=[C:14]([CH3:35])[C:13]=1[OH:36])C.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:33]([N:31]([CH2:30][C:25]1[CH:24]=[C:23]([C:21]2[O:20][N:19]=[C:18]([C:16]3[CH:15]=[C:14]([CH3:35])[C:13]([O:36][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])=[C:12]([CH3:10])[CH:17]=3)[N:22]=2)[CH:28]=[C:27]([CH3:29])[CH:26]=1)[CH3:32])[CH3:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 136331245HCID 136331245, compound

Product 1

HCID 66932107HCID 66932107, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

4-bromobutyl acetate (186 mg, 936 μmol) was added to a suspension of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (114 mg, 312 μmol) and K2CO3 (129 mg, 936 μmol) in acetonitrile (2 mL). The mixture was stirred at 70° C. for 2 h before it was filtered. The filtrate was diluted with 25% aq. ammonia (0.5 mL) and a 32% aq. NaOH solution (300 μL) and the bi-phasic mixture was stirred at 70° C. for 2 h. The aq. phase was separated and 1N aq. NaOH (0.4 mL) was added. The now homogenous mixture was separated by prep. HPLC (XBridge 30×75 mm, eluting with a gradient of MeCN in water containing 0.5% of sat. aq. ammonia) to give the title compound as a white lyophilisate (53 mg). LC-MS: tR=0.65 min; [M+1]+=438.25; 1H NMR (D6-DMSO): δ 1.06 (t, J=7.0 Hz, 3H), 1.23 (t, J=7.5 Hz, 3H), 1.61-1.69 (m, 2H), 1.78-1.86 (m, 2H), 2.15 (s, 3H), 2.34 (s, 3H), 2.41-2.48 (m, 5H), 2.71 (q, J=7.5 Hz, 2H), 3.47-3.53 (m, 2H), 3.55 (s, 2H), 3.81-3.86 (m, 2H), 4.47 (br s, 1H), 7.47 (s, 1H), 7.80 (s, 2H), 7.90 (s, 1H), 7.93 (s, 1H).

Workup

  1. filtrationwas filtered
  2. additionThe filtrate was diluted with 25% aq. ammonia (0.5 mL)
  3. stirringa 32% aq. NaOH solution (300 μL) and the bi-phasic mixture was stirred at 70° C. for 2 h
  4. customThe aq. phase was separated
  5. addition1N aq. NaOH (0.4 mL) was added
  6. customThe now homogenous mixture was separated by prep
  7. washHPLC (XBridge 30×75 mm, eluting with a gradient of MeCN in water containing 0.5% of sat. aq. ammonia)

Sources & evidence

ORD record
ord-e6b6fe6a9da840b79119b645cecf7037
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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