1,1,1-Trimethoxybutane → HCID 21912924, compound

HRID 1352543Notes

Reaction equation

HRID 1352543 reaction equation
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH3:4].[CH2:11]([O:18][CH2:19][CH2:20][NH:21][C:22]1[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=[C:24]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:23]=1[NH2:37])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1.Cl.N1C=CC=CC=1>[CH2:11]([O:18][CH2:19][CH2:20][N:21]1[C:22]2[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=[C:24]([O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:23]=2[N:37]=[C:1]1[CH2:2][CH2:3][CH3:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 1235121,1,1-TrimethoxybutaneHCID 21226206Ethyl acetate hexaneHCID 86596478HCID 86596478, compound

Product 1

HCID 21912924HCID 21912924, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Pyridine hydrochloride (0.04 g, 0.380 mmol), and trimethyl orthobutyrate (4.6 mL, 28.48 mmol) were added to a stirred solution of N4-[2-(benzyloxy)ethyl]-5,6-dimethyl-2-phenoxypyridine-3,4-diamine (6.9 g, 18.984 mmol) prepared as in Part E of Example 4 in toluene (65 mL). After the resulting solution was heated to reflux for 2 hours, the reaction was complete as determined by TLC (using 1/1 hexane/ethyl acetate), HPLC, and LC/MS. The reaction solution was then concentrated under reduced pressure, and the resulting oil was dissolved in ethyl acetate. The ethyl acetate solution was washed with brine (3×), dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting tan solids were triturated with diethyl ether, filtered off, and dried to provide 6.5862 g of pure product (by NMR and LC/MS), which was used in the next step.

Workup

  1. temperatureAfter the resulting solution was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction solution was then concentrated under reduced pressure
  4. dissolutionthe resulting oil was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with brine (3×)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting tan solids were triturated with diethyl ether
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-1341c3cba73d4f3b86331631908104d5
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

Loading…