Ammonium Hydroxide → HCID 19427668, compound

HRID 1078543Notes

Reaction equation

HRID 1078543 reaction equation
[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](OS(C(F)(F)F)(=O)=O)=[N:7][C:6]3[C:23]([CH3:27])=[CH:24][CH:25]=[N:26][C:5]2=3)[CH2:3][CH2:2]1.[OH-].[NH4+:29]>O1CCOCC1.C(OCC)(=O)C>[NH2:29][C:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=2[N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]2[N:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 19427680HCID 19427680, compound

Product 1

HCID 19427668HCID 19427668, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 11-cyclopropyl-4-methyl-6-trifluoromethanesulfonyloxy-11H-dipyrido[3,2-b:2',3'-e][1,4]diazepine (0.22 g, 0.55 mmol) in 1,4-dioxane (3 mL) was added 30% ammonium hydroxide (3 mL). The mixture was heated at 100° C. for 15 min. After cooling to room temperature the mixture was diluted with ethyl acetate, washed with water, dried (magnesium sulfate), filtered and concentrated in vacuo. The residue was chromatographed over silica gel (eluted with 1:1:1 ethyl acetate/hexane/methylene chloride→50% ethyl acetate/hexane) to give the title compound (0.045 g, 0.17 mmol, 30%) which crystallized from ethyl acetate/hexane, m.p. 242°-244° C.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over silica gel (eluted with 1:1:1 ethyl acetate/hexane/methylene chloride→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-09ceb7c8182a42de9faab1031432f103
Source dataset
uspto-grants-1996_08
Patent number
US05550117

Reaction notes

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