Sodium Azide → HCID 25141631, compound

HRID 549367Notes

Reaction equation

HRID 549367 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@:10]2([CH2:27][N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)[O:14][C@H:13]([CH2:15]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][O:11]2)=[CH:4][CH:3]=1.[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C)C=O.O>[N:33]([CH2:15][CH:13]1[CH2:12][O:11][C:10]([CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[O:14]1)=[N+:34]=[N-:35]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 10994419HCID 10994419, compound

Product 1

HCID 25141631HCID 25141631, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of QC-16 (201 mg, 0.42 mmol) in N,N-dimethylformamide (3 mL) was added sodium azide (546 mg, 8.40 mmol, 20 equiv). The mixture was heated at 110° C. with stirring for 2 h. The reaction mixture was cooled to room temperature, diluted with H2O, extracted with EtOAc (3×), and the combined organic extracts were washed sequentially with a saturated aqueous solution of Na2CO3, and 1120, and then dried (Na2SO4). The solution was concentrated and the golden oily residue purified by flash column chromatography on silica gel (EtOAc) to give the free base as an oil (Rf=0.29, EtOAc). High-vacuum drying left 121 mg (0.35 mmol, 83%) of QC-112 as a colorless oil: [α]D24=+6.6° (c=0.7, CDCl3); 1H NMR (400 MHz, CDCl3): δ 1.90-2.05 (m, 2H), 2.66-2.81 (m, 2), 3.20 (dd, J=13.2, 5.2 Hz, 1H), 3.39 (dd, J=13.2, 4.0 Hz, 1H), 3.44-3.51 (m, 1H), 3.64 (t, J=8.0 Hz, 1H), 3.78 (dd, J=8.0, 6.4 Hz, 1H), 4.02 (s, 2H), 6.98 (br s, 1H), 7.05 (br s, 1H), 7.12 (d, J=8.4 Hz, 2H), 7.25 (d, J=8.4 Hz, 2H), 7.49 (br s, 1H); 13C NMR (100 MHz, CDCl3): δ 29.0, 38.7, 51.8, 53.0, 67.9, 76.1, 109.9, 120.9, 128.8, 129.3, 129.8, 132.1, 138.7, 139.6; HRMS (EI) [M+H]+ Calcd. for C16H19ClN5O2: 348.1227. Found: 348.1234.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washthe combined organic extracts were washed sequentially with a saturated aqueous solution of Na2CO3, and 1120
  4. dry with materialdried (Na2SO4)
  5. concentrationThe solution was concentrated
  6. customthe golden oily residue purified by flash column chromatography on silica gel (EtOAc)
  7. customto give the free base as an oil (Rf=0.29, EtOAc)
  8. customHigh-vacuum drying
  9. waitleft 121 mg (0.35 mmol, 83%) of QC-112 as a colorless oil

Sources & evidence

ORD record
ord-e171c0b6c5034eea820a88a8792d1fd5
Source dataset
uspto-grants-2011_05
Patent number
US07943650B2

Reaction notes

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