HCID 178507773, compound → HCID 178432225, compound

HRID 1890286Notes

Reaction equation

HRID 1890286 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(NC2N=C(O)C=CC=2[N+]([O-])=O)CCCCC[CH2:18]1>CC(C)(C)C([O-])([O-])[O-]>[CH:9]1([N:8]2[C:7]3=[N:6][C:5]([OH:16])=[CH:4][CH:3]=[C:2]3[N:1]=[C:17]2[CH3:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 178507773HCID 178507773, compoundHCID 178526706HCID 178526706, compound

Product 1

HCID 178432225HCID 178432225, compound

Reagents, catalysts & solvents 1

HCID 21927715TrimethylorthoacetateSolvent

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, was taken up in trimethylorthoacetate and stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give the title compound. LCMS m/z=246.1 [M+H]+; 1H NMR (400 MHz, acetonitrile-d3) δ ppm 1.55-1.80 (m, 6H), 1.85-2.05 (m, 4H), 2.50-2.60 (m, 2H), 2.80 (s, 3H), 4.50-4.60 (m, 1H), 6.84 (d, J=8.8 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-58422096f2e9463f94eb0bdc8db5b2ad
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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