Hydrochloric Acid → 11-ethyl-5,11-dihydro-8-[2-(4-amino-2-methylphenoxy)ethyl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 393297Notes

Reaction equation

HRID 393297 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23]C(=O)OC(C)(C)C)=[CH:19][C:18]=3[CH3:31])=[CH:13][C:8]=2[C:7](=[O:32])[N:6]([CH3:33])[C:5]2[CH:34]=[CH:35][CH:36]=[N:37][C:4]1=2)[CH3:2].Cl.O1CCOCC1>>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=3[CH3:31])=[CH:13][C:8]=2[C:7](=[O:32])[N:6]([CH3:33])[C:5]2[CH:34]=[CH:35][CH:36]=[N:37][C:4]1=2)[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 226488701,1-Dimethylethyl n-{4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methylphenyl}carbamate

Product 1

HCID 2264885811-ethyl-5,11-dihydro-8-[2-(4-amino-2-methylphenoxy)ethyl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 92.2%

Conditions

Temperature
25 °C

Procedure

A mixture of 1,1-dimethylethyl N-{4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-8-yl)ethoxy]-3-methylphenyl}carbamate (540 mg, 1.07 mmol) and 4 N HCl in 1,4-dioxane (5.0 mL, 20 mmol) was stirred at 25° C. for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was taken in water (6 mL) and the resulting solution was washed with EtOAc. The aqueous layer was rendered basic (pH 9) with aqueous 2 N NaOH solution and the mixture was extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure to yield the title compound (398 mg, 92% yield) as a beige foam.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe resulting solution was washed with EtOAc
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4aadd1f99a345b0bdb0ddb15aa4a63c
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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