Triethylamine → HCID 178458527, compound

HRID 1644598Notes

Reaction equation

HRID 1644598 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:25][CH:26]([CH3:28])[CH3:27])=[C:13]([C:15]2[NH:24][C:18]3=[N+:19]([O-])[CH:20]=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]([N:31](CC)CC)C.C[Si](C#N)(C)C>C(#N)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:25][CH:26]([CH3:28])[CH3:27])=[C:13]([C:15]2[NH:24][C:18]3=[N:19][C:20]([C:29]#[N:31])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 178458532HCID 178458532, compound

Product 1

HCID 178458527HCID 178458527, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution (10 ml) of 2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridine 4-oxide, triethylamine (0.11 g) and trimethylsilyl cyanide (0.22 g) in acetonitrile was heated under reflux for 5 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. The obtained crude crystals were washed with diethyl ether to give the title compound (0.15 g, yield 69%) as colorless crystals. melting point 214-215° C. purity 93%. M+H: 385. 1H NMR (CDCl3) δ: 1.53 (6H, d, J=6.0 Hz), 4.77-4.85 (1H, m), 5.16 (2H, s), 7.06 (1H, d, J=9.0 Hz), 7.12-7.18 (1H, m), 7.32-7.50 (5H, m), 7.66 (1H, d, J=8.1 Hz), 8.12 (1H, d, J=8.1 Hz), 8.20 (1H, d, J=3.0 Hz).

Workup

  1. temperatureunder reflux for 5 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained crude crystals
  7. washwere washed with diethyl ether

Sources & evidence

ORD record
ord-915badedabbd465095ddfb402e101fa4
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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