Diisopropylethylamine → HCID 178462462, compound

HRID 2380252Notes

Reaction equation

HRID 2380252 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7](OS(C)(=O)=O)[NH:6][C:5]2[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[N:22][C:4]1=2)[CH3:2].Cl.[O:26]([NH2:28])[CH3:27].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[N:28][O:26][CH3:27])[NH:6][C:5]2[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[N:22][C:4]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 199600595,11-Dihydro-11-ethyl-6-methanesulfonyloxy-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine

Product 1

HCID 178462462HCID 178462462, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5,11-dihydro-11-ethyl-6-methanesulfonyloxy-2,4-dimethyl-6H-dipyrido[3,2-b:2',3'-e] [1,4]diazepine (0.3 g, 0.75 mmol), methoxylamine hydrochloride (0.15 g, 1.8 mmol) and diisopropylethylamine (0.3 g, 2 mmol) in methylene chloride was stirred at room temperature for 4 days. The organic phase was washed with water, dried, and filtered. The solution was concentrated in vacuo and the residue was chromatographed over silica with 20% ethyl acetate/hexane to give 0.07 g of the title compound, m.p. 164°-166° C.

Workup

  1. washThe organic phase was washed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationThe solution was concentrated in vacuo
  5. customthe residue was chromatographed over silica with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2ab211cc17d74258bb5a7d728e0d8f23
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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