Acetaldehyde → HCID 57742631, compound

HRID 911915Notes

Reaction equation

HRID 911915 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:7]=[C:8]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[N:14]=2)=[N:10][CH:11]=1.C[Li].C([Li])CCC.[CH:42](=[O:44])[CH3:43].[NH4+].[Cl-]>C1COCC1>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([S:23][C:8]2[CH:7]=[C:6]([O:5][C:4]3[CH:3]=[C:2]([CH:42]([OH:44])[CH3:43])[CH:34]=[CH:33][CH:32]=3)[CH:11]=[N:10][C:9]=2[NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[N:14]=2)[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 25517Ammonium ChlorideHCID 57742918HCID 57742918, compoundHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 57742631HCID 57742631, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A 10 mL round-bottomed flask was charged with 5-(3-bromophenoxy)-3-(3-methoxyphenylthio)-N-(3-(tetrahydrofuran-2-yl)-1,2,4-thiadiazol-5-yl)pyridin-2-amine (43.3 mg, 0.077 mmol) and THF (2 mL). The reaction was cooled to −78° C. and methyllithium (0.058 mL, 0.093 mmol) was added and stirred for 5 min. Butyllithium (0.037 mL, 0.093 mmol) was added and the reaction was stirred for 5 min. Acetaldehyde (0.0086 mL, 0.16 mmol) was added and the reaction warmed to room temperature and poured into saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (35 to 100% ethyl acetate in hexanes) to afford the title compound (4.5 mg, 11.1% yield). 1H NMR (CDCl3) δ 9.26 (bs, 1H), 8.25 (d, 1H), 7.63 (d, 1H), 7.33 (t, 1H), 7.21 (t, 1H), 7.14 (d, 1H), 7.05 (m, 1H), 6.90 (dd, 1H), 6.76 (m, 2H), 6.70 (m, 1H), 4.89 (q, 1H), 4.15 (t, 1H), 4.03 (m, 2H), 3.90 (m, 1H), 3.77 (s, 3H), 3.64 (m, 1H), 2.34 (q, 2H), 1.47 (d, 3H). Mass spectrum (apci) m/z=523.2 (M+H).

Workup

  1. stirringthe reaction was stirred for 5 min
  2. temperaturethe reaction warmed to room temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (35 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7d955068852b4cc395520833af14faa5
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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