Cyanogen Bromide → HCID 178508196, compound

HRID 1890285Notes

Reaction equation

HRID 1890285 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[N:6][C:7]=1[NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH:17]1([NH:24]C2N=C(O)C=CC=2[N+]([O-])=O)CCCCCC1.N#CBr>C(O)C>[NH2:24][C:17]1[N:8]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:7]2=[N:6][C:5]([OH:16])=[CH:4][CH:3]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 178507773HCID 178507773, compoundHCID 178526706HCID 178526706, compound

Product 1

HCID 178508196HCID 178508196, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Amino-6-(cycloheptylamino)pyridin-2-ol, prepared in a similar manner as the one described in Example 1.3 from 6-(cycloheptylamino)-5-nitropyridin-2-ol (0.225 g, 0.895 mmol), was taken up in ethanol (20 mL). Cyanogen bromide (0.153 g, 1.34 mmol) was then added. The resulting solution was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was purified by preparative HPLC to give the title compound (0.004 g). LCMS m/z=247.0 [M+H]+; 1H NMR (400 MHz, acetonitrile-d3) δ ppm 1.50-1.80 (m, 6H), 1.80-2.05 (m, 4H), 2.45-2.55 (m, 2H), 4.25-4.35 (m, 1H), 6.55 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.5 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1a54d0acffcf4ed7aedc6e5fb348fed8
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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