HCID 18696600, compound → HCID 18696622, compound

HRID 1870544Notes

Reaction equation

HRID 1870544 reaction equation
[CH3:1][O:2][C:3]1[N:7]([C:8]2[C:9]([C:13](OC)=[O:14])=[CH:10][O:11][CH:12]=2)[C:6](=[O:17])[N:5]([CH3:18])[N:4]=1.[H-].C([Al+]CC(C)C)C(C)C.CO.C(OCC)(=O)C>C(Cl)Cl.CC(C)=O>[OH:14][CH2:13][C:9]1[C:8]([N:7]2[C:3]([O:2][CH3:1])=[N:4][N:5]([CH3:18])[C:6]2=[O:17])=[CH:12][O:11][CH:10]=1

Participants

6

Reactant 3

HCID 18696600HCID 18696600, compoundHCID 21225700DiisobutylaluminumhydrideHCID 21584119Ethylacetate methanol

Product 1

HCID 18696622HCID 18696622, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the title compound of Step E (4.6 g) in methylene chloride (40 mL) under nitrogen was cooled to -78° C. while stirring. A solution of diisobutylaluminum hydride (55.0 mL, 1 M in CH2Cl2) in methylene chloride was then added, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction was monitored by TLC (5% methanol/ethyl acetate). After cooling back down to -78° C., the reaction was diluted with acetone (45 mL), quenched with glacial acetic acid (20 mL) and then allowed to warm to room temperature. The resulting mixture was further diluted with water (200 mL) and extracted successively with methylene chloride and ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to yield 3.62 g of the title compound of Step F as an orange solid melting at 132.5-133.5° C. 1H NMR (CDC3): δ 7.53 (s,2H), 4.38 (s,3H), 3.99 (s,3H), 3.44 (s,3H).

Workup

  1. stirringstirred for 1 h
  2. temperatureAfter cooling back down to -78° C.
  3. customquenched with glacial acetic acid (20 mL)
  4. temperatureto warm to room temperature
  5. additionThe resulting mixture was further diluted with water (200 mL)
  6. extractionextracted successively with methylene chloride and ethyl acetate
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03c3f57e89c14491a32caaa0d85256d3
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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