Aminoacetaldehyde dimethyl acetal → HCID 178495872, compound

HRID 575039Notes

Reaction equation

HRID 575039 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([N:9]=[C:10]2Cl)[CH2:7]3)=[CH:4][C:3]=1[F:15].[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][NH2:20]>CCCCO.O>[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([N:9]=[C:10]2[NH:20][CH2:19][CH:18]([O:21][CH3:22])[O:17][CH3:16])[CH2:7]3)=[CH:4][C:3]=1[F:15]

Participants

5

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 86693069HCID 86693069, compound

Product 1

HCID 178495872HCID 178495872, compoundYield 107.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Into a 100-mL 3-necked round-bottom flask was placed a solution of 5-bromo-8-chloro-4-fluoro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraene (3.75 g, 13.00 mmol, 1.00 equiv) in n-BuOH (50 mL) and 2,2-dimethoxyethan-1-amine (1.5 g, 14.27 mmol, 1.10 equiv). The resulting solution was stirred at 100° C. for 1.5, diluted with 50 mL of water and extracted with 1×50 mL of ethyl acetate. The organic layers were combined and concentrated under vacuum to afford 5.0 g (crude) of 5-bromo-N-(2,2-dimethoxyethyl)-4-fluoro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraen-8-amine as a yellow oil.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask was placed
  2. extractionextracted with 1×50 mL of ethyl acetate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1340da24d82244e1a381053ad78141d0
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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