HCID 59841049, compound → HCID 178423961, compound

HRID 874907Notes

Reaction equation

HRID 874907 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:38])[N:5]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:6]([CH:12]([O:14][C:15]1[N:23]=[CH:22][N:21]=[C:20]3[C:16]=1[N:17]=[CH:18][N:19]3COCC[Si](C)(C)C)[CH3:13])=[N:7]2>CO.Cl>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:38])[N:5]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:6]([CH:12]([O:14][C:15]1[N:23]=[CH:22][N:21]=[C:20]3[C:16]=1[N:17]=[CH:18][NH:19]3)[CH3:13])=[N:7]2

Participants

4

Reactant 1

HCID 59841049HCID 59841049, compound

Product 1

HCID 178423961HCID 178423961, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Compound 182 (0.053 g, 0.1 mmol) was dissolved in a mixture of methanol (2 mL) and 4M HCl (2 mL). The mixture was stirred and heated to 40° C. for 3 h. The reaction mixture was removed from the heat source and allowed to cool. The reaction mixture was then filtered through a plug of GFA (glass fiber) filter paper and the filtrate concentrated to only remove the methanol. The residue was adjusted to pH 10 by addition of 10% potassium carbonate solution. The resulting solid was collected by filtration and purified by RP-HPLC (C18 Luna column, 10×250 mm, 4.7 mL/min, 10-90% CH3CN in water in 18 min, with all solvents containing 0.05% formic acid) to give compound 176 as a fluffy white solid after lyophilization. 1H NMR (400 MHz, d6-DMSO) δ13.40, br s, 1H; 8.40, s, 1H; 8.35, s, 1H; 7.66, t, J=7.8 Hz, 1H; 7.48-7.58, m, 4H; 7.31-7.36, m, 2H; 7.20-7.23, m, 1H; 5.65, q, J=6.6 Hz, 1H; 2.73, s, 3H; 1.65, d, J=6.6 Hz, 3H. ESI-MS m/z=399 (MH+). The reaction described above and compound 176 are shown below.

Workup

  1. customThe reaction mixture was removed from the heat source
  2. temperatureto cool
  3. filtrationThe reaction mixture was then filtered through a plug of GFA (glass fiber)
  4. filtrationfilter paper
  5. concentrationthe filtrate concentrated
  6. customto only remove the methanol
  7. additionThe residue was adjusted to pH 10 by addition of 10% potassium carbonate solution
  8. filtrationThe resulting solid was collected by filtration
  9. custompurified by RP-HPLC (C18 Luna column, 10×250 mm, 4.7 mL/min, 10-90% CH3CN in water in 18 min
  10. additionwith all solvents containing 0.05% formic acid)

Sources & evidence

ORD record
ord-5be9d374dab64e7aa34f187d90033722
Source dataset
uspto-grants-2015_03
Patent number
US08980901B2

Reaction notes

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