Sodium Azide → HCID 178520586, compound

HRID 852875Notes

Reaction equation

HRID 852875 reaction equation
[CH2:1]([O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][C@@H:14]([NH:19][C:20](=[O:33])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:15][CH2:16][C:17]#[N:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:36]=[N+:37]=[N-:38].[Na+].N(CC)CC.Cl>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][C@@H:14]([NH:19][C:20](=[O:33])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:15][CH2:16][C:17]2[NH:38][N:37]=[N:36][N:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 10197650Diethylammonium chlorideHCID 90837799HCID 90837799, compound

Product 1

HCID 178520586HCID 178520586, compoundYield 219.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (65) (74 mg, 0.16 mmol), NaN3 (103 mg, 1.58 mmol) and Et2NH.HCl (173 mg, 1.58 mmol) in toluene (1.5 mL) was heated at reflux for 48 h. The organic phase was decanted, and the remaining gum washed several times with CH2Cl2. The washings were filtered (Celite™), and the organic phases combined. Evaporation of the solvent under reduced pressure afforded a brown gum (180 mg) which was chromatographed on a C-18 reverse phase column to provide (66) (29 mg, 36%). 1H NMR (500 MHz, d4-MeOH) δ 7.43-7.07 (m, 12H), 6.9 (d, 2H, J=8.6 Hz), 4.99 (s, 2H), 4.15-4.04 (m, 1H), 3.03-2.86 (m, 2H), 2.79 (dd, 1H, J=5.7, 13 Hz), 2.65 (dd, 1H, J=8.7, 13 Hz), 2.54 (t, 2H, J=7.6 Hz), 2.12-2.00 (m, 3H), 1.90-1.78 (m, 1H), 1.50-1.36 (m, 2H), 1.33-1.10 (m, 4H). 13C NMR (125 MHz, d4-MeOH) δ 176.2, 158.9, 156.2, 143.9, 138.8, 131.9, 131.3, 129.5, 129.4, 129.3, 128.8, 128.5, 126.6, 115.8, 71.0, 51.5, 41.1, 37.2, 36.8, 33.5, 32.5, 30.0 (two superimposed), 27.0, 21.3. ESMS 512 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. customThe organic phase was decanted
  4. washthe remaining gum washed several times with CH2Cl2
  5. filtrationThe washings were filtered (Celite™)
  6. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-65b1b5a9d4c144caa1d89b1a4573242f
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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