Ethyl Acetate → HCID 57906609, compound

HRID 420504Notes

Reaction equation

HRID 420504 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]=[C:11]([NH:23][NH2:24])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:27]#[N:28].CCOC(C)=O>CCO>[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:27]([NH2:28])=[N:24][N:23]=[C:11]2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 57906562HCID 57906562, compound

Product 1

HCID 57906609HCID 57906609, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of the crude [5-(2,4-dichloro-phenyl)-2-hydrazino-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester (1.66 g) and BrCN (638 mg, 6.0 mmol) in EtOH (40 mL) was heated at 65° C. and stirred for 2 h30. The reaction mixture was cooled to RT, poured into AcOEt (100 mL) and washed with a 2.0 M aqueous Na2CO3 solution (2×50 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 95:5→4:6) to yield the title compound (908 mg, 2.22 mmol, 74% over 2 steps) as a brownish solid. MS: 408 [M+1]+; HPLC: AtRet=1.62; TLC: RF 0.16 (DCM/MeOH 95:5).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with a 2.0 M aqueous Na2CO3 solution (2×50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 95:5→4:6)

Sources & evidence

ORD record
ord-6511319e98634cbdbaf901d6da5cdc68
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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