Cyanogen Bromide → HCID 178436509, compound

HRID 1890330Notes

Reaction equation

HRID 1890330 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([NH2:24])=[CH:11][CH:10]=1)C1C=CC=CC=1.[N:25]#[C:26]Br.C([O-])(O)=O.[Na+].C([O-])=O.[NH4+]>[Pd].O>[NH2:25][C:26]1[N:15]([C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=2)[C:13]2=[N:14][C:9]([OH:8])=[CH:10][CH:11]=[C:12]2[N:24]=1

Participants

7

Reactant 4

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 2723923Ammonium formateHCID 67312934HCID 67312934, compound

Product 1

HCID 178436509HCID 178436509, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To 6-(benzyloxy)-N2-(4-ethylphenyl)pyridine-2,3-diamine (358 mg, 1.12 mmol) was added H2O (3.0 mL) and cyanogen bromide (178 mg, 1.68 mmol). The mixture was stirred vigorously at room temperature overnight. Saturated NaHCO3 was added and the mixture was extracted with EtOAc. After concentration in vacuo, the crude material was dissolved in MeOH (5 mL) and ammonium formate (353 mg, 5.6 mmol) was added. Pd/C (10% by wt., 100 mg) was added and the mixture was stirred in a sealed vial at 60° C. overnight. The reaction mixture was cooled to room temperature, filtered through celite, and concentrated. The residue was purified by preparative HPLC to give the title compound (14.4 mg) as a white solid. LCMS m/z=255.3, [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (t, J=7.6 Hz, 3H), 2.73 (q, J=7.6 Hz, 2H), 6.54 (d, J=8.5 Hz, 1H), 7.49 (d, J=8.5 Hz, 2H), 7.53 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.5 Hz, 1H), 8.32 (broad s, 2H), 10.91 (broad s, 1H).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe crude material was dissolved in MeOH (5 mL)
  4. stirringthe mixture was stirred in a sealed vial at 60° C. overnight
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationfiltered through celite
  7. concentrationconcentrated
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ef3411d3c9b94c3b90fa867cf6632b13
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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