Pyridine → HCID 67789353, compound

HRID 1654004Notes

Reaction equation

HRID 1654004 reaction equation
N1C=CC=CC=1.[CH2:7]([Si:9]([CH2:13][CH3:14])([CH2:11][CH3:12])Cl)[CH3:8].[OH:15][C@@H:16]([C@@H:18]1[C@@H:21]([C@H:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[NH:20][C:19]1=[O:33])[CH3:17]>C(Cl)Cl>[CH2:7]([Si:9]([CH2:13][CH3:14])([CH2:11][CH3:12])[O:15][C@@H:16]([C@@H:18]1[C@@H:21]([C@H:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[NH:20][C:19]1=[O:33])[CH3:17])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13819ChlorotriethylsilaneHCID 67906298HCID 67906298, compound

Product 1

HCID 67789353HCID 67789353, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.06 ml of pyridine and 0.1 ml of triethylchlorosilane were added successively at 0° C. to 100 mg (0.39 mmol) of the hydroxyethyl compound from step 1 in 3 ml of anhydrous methylene chloride and then stirred at room temperature for 3 h. The reaction mixture was diluted with 10 ml of methylene chloride and washed successively with dilute hydrochloric acid, saturated NaHCO3 solution and water. After drying over sodium sulfate and concentration in vacuo, the residue was chromatographed on silica gel (eluent: toluene/ethyl acetate=1:2). Yield: 122 mg (85%). -1H-NMR (200 MHz, CDCl3): δ=0.50-0.70 (2×m, 6H and 9H, SiCH3CH3); 1.28 (d, 3H, CH--CH3); 1.95-2.38 (m, 2H, CH--CH2 --CH2); 2.76 (dt, 1H, CH--CH2 --CH2) 3.02-3.16 (m, 3H, CH--CH2 --CH2 and H-3); 4.23 (mc, 1H, CH--CH3); 4.43 (dd, 1H, H-4); 5.8 (bs, 1H, NH); 7.22-7.38 and 7.45-7.57 (2×m, 3 H, aromatic H); 8.02 (dd, 1H, aromatic H).

Workup

  1. washwashed successively with dilute hydrochloric acid, saturated NaHCO3 solution and water
  2. dry with materialAfter drying over sodium sulfate and concentration in vacuo
  3. customthe residue was chromatographed on silica gel (eluent: toluene/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-156cdb32df2c4f8aa2aa18288a331151
Source dataset
uspto-grants-1995_04
Patent number
US05405844

Reaction notes

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