Silicon tetrachloride → HCID 70496202, compound

HRID 2408045Notes

Reaction equation

HRID 2408045 reaction equation
Cl[Si](Cl)(Cl)Cl.[N-:6]=[N+:7]=[N-:8].[Na+].[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31](=O)[NH:32][CH:33]3[CH2:35][CH2:34]3)[CH:26]=1)[CH2:19][C:18]2([CH3:38])[CH3:37])=[O:14])[CH3:11]>C(#N)C>[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]3[N:32]([CH:33]4[CH2:34][CH2:35]4)[N:8]=[N:7][N:6]=3)[CH:26]=1)[CH2:19][C:18]2([CH3:37])[CH3:38])=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 70496987HCID 70496987, compound

Product 1

HCID 70496202HCID 70496202, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tetrachlorosilane (5.3 mL, 46.3 mmol), sodium azide (5.6 g, 87 mmol) in dry acetonitrile (20 mL) was added 2-(3-cyclopropylcarbamoyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.3 g, 3.3 mmol) at room temperature. Then the mixture solution was stirred at room temperature for over night. LC/MS showed that reaction finished completely. The reaction mixture was poured into ice-cold saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (150 mL×2), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (30% ethyl acetate/hexanes) afforded 2-[3-(1-cyclopropyl-1H-tetrazol-5-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (908.2 mg, 66%) as a white solid: MS (ESI) M+1=418.1.

Workup

  1. customLC/MS showed that reaction
  2. additionThe reaction mixture was poured into ice-cold saturated aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (150 mL×2)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ba3401b7e80c4c56b99ed222fdd6e7a8
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

Loading…