Sodium Azide → HCID 86668681, compound

HRID 341079Notes

Reaction equation

HRID 341079 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:37](=[O:38])[C:16]2=[CH:17][N:18]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:36]=[CH:35][CH:34]=[N:33]4)=[CH:28][CH:27]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:15]2=[N:14]1)(=O)=O.[N-:39]=[N+:40]=[N-:41].[Na+].C(=O)(O)[O-].[Na+]>CS(C)=O>[N:39]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:37](=[O:38])[C:16]2=[CH:17][N:18]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:36]=[CH:35][CH:34]=[N:33]4)=[CH:28][CH:27]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:15]2=[N:14]1)=[N+:40]=[N-:41]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 86668680HCID 86668680, compound

Product 1

HCID 86668681HCID 86668681, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[2-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)phenyl]methyl methanesulfonate (0.21 g, 0.51 mmol) was dissolved in dimethyl sulfoxide (10 mL) and treated with sodium azide (0.33 g, 5.1 mmol, 10 equiv). The mixture was stirred for 45 minutes at ambient temperature and then placed into a preheated oil bath at 80° C. for 1 hour. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (100 mL, aqueous saturated) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 5% methanol), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.17 (1H, s), 8.46 (1H, d, J=2.5 Hz), 8.23 (1H, d, J=7.8 Hz), 7.83 (2H, d, J=8.6 Hz), 7.79 (1H, d, J=8.6 Hz), 7.72 (1H, m), 7.65-7.61 (1H, m), 7.57-7.54 (3H, m), 7.51 (1H, br d, J=7.6 Hz), 7.49-7.45 (3H, m), 6.53 (1H, m), 5.78 (2H, s), 4.60 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 473.1823 [(M+H)+; calculated for C27H21N8O: 473.1833].

Workup

  1. waitplaced into a preheated oil bath at 80° C. for 1 hour
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 5% methanol)

Sources & evidence

ORD record
ord-efdf801dada54024a1c19dd8062bd29a
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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