Hydrogen Bromide → HCID 90310921, compound

HRID 527201Notes

Reaction equation

HRID 527201 reaction equation
[CH:1]([N:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[C:13]([F:31])[CH:12]=2)[CH:7]=[N:6]1)([CH2:3][CH3:4])[CH3:2].Br.C([O-])([O-])=O.[Na+].[Na+]>>[CH:1]([N:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23]4[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=4)[CH2:21][CH2:22]3)=[C:13]([F:31])[CH:12]=2)[CH:7]=[N:6]1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 71295313HCID 71295313, compound

Product 1

HCID 90310921HCID 90310921, compoundYield 84.5%

Conditions

Temperature
120 °C

Procedure

Triazolone 8 (0.1 g, 0.23 mmol) was added to aqueous HBr (48%, 1.9 mL). The reaction was heated to 120° C. and refluxed overnight. The reaction mixture was cooled to room temperature and the solution was neutralized with saturated Na2CO3 and extracted with dichloromethane (DCM). The combined organic layer was dried (Na2SO4), filtered, and concentrated to yield the product, which was purified by column chromatography to obtain compound 9 (0.08 g, 83%). 1H NMR (400 MHz, CDCl3, δH): 7.57 (s, 1H), 7.24 (dd, J=10.2, 2.0 Hz, 1H), 7.15 (dd, J=6.8, 1.6 Hz, 1H), 6.92 (t, J=7.0 Hz, 1H), 6.79 (d, J=6.8 Hz, 2H), 6.67 (d, J=7.2 Hz, 2H), 4.24-4.20 (m, 1H), 3.17-3.16 (m, 8H), 1.82-1.77 (m, 1H), 1.66-1.63 (m, 1H), 1.32 (d, J=5.6 Hz, 3H), 0.82 (t, J=5.8 Hz, 3H). 13C NMR (100 MHz, CDCl3, δC): 156.3, 154.3, 150.8, 144.9, 139.7, 133.6, 127.8, 119.4, 118.9, 116.0, 111.4, 53.1, 51.2, 50.5, 28.4, 19.3, 10.8.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with dichloromethane (DCM)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield the product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6230a40eabb94fd496064d505c321cf6
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

Loading…