Hydrochloric Acid → HCID 23135143, compound

HRID 475509Notes

Reaction equation

HRID 475509 reaction equation
[CH2:1]([N:8]1[C:12]2[CH2:13][CH:14]([O:16][CH2:17][CH2:18][CH3:19])[CH2:15][C:11]=2[C:10]([C:20]#[N:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[N-:23]=[N+:24]=[N-:25].[Na+].Cl>CC(O)C.[Br-].[Zn+2].[Br-]>[CH2:1]([N:8]1[C:12]2[CH2:13][CH:14]([O:16][CH2:17][CH2:18][CH3:19])[CH2:15][C:11]=2[C:10]([C:20]2[N:23]=[N:24][NH:25][N:21]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 33557Sodium AzideHCID 23135147HCID 23135147, compound

Product 1

HCID 23135143HCID 23135143, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the intermediate from step A (25 mg, 0.089 mmol) in 2-propanol (1 mL) was added water (2 mL), sodium azide (14 mg, 0.222 mmol) and zinc bromide (10 mg, 0.04 mmol). After heating the reaction mixture at 90° C. for 18 hours, it was cooled to room temperature and HCl (3 mL, 3N) was added. The reaction mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous Na2SO4 filtered and concentrated in vacuo. The residue was purified by PTLC (SiO2) using 100% ethyl acetate to give the desired product.

Workup

  1. temperatureit was cooled to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by PTLC (SiO2)

Sources & evidence

ORD record
ord-4791c1441f4b438c9d8e918ea54f76a7
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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