Methyl 2-aminopyridine-3-carboxylate → HCID 178515099, compound

HRID 1951052Notes

Reaction equation

HRID 1951052 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([OH:14])[CH:10]=[C:11](O)[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.C[O:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][C:31]=1[NH2:36]>C(O)CCCCC>[OH:14][C:9]1[C:10]2[C:29](=[O:28])[C:30]3[CH:35]=[CH:34][CH:33]=[N:32][C:31]=3[NH:36][C:11]=2[CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH:8]=1

Participants

5

Reactant 3

HCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58923367HCID 58923367, compound

Product 1

HCID 178515099HCID 178515099, compoundYield 2.1%

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Procedure

5-Morpholin-4-yl-benzene-1,3-diol (345 mg 1.77 mmol), TsOH.H2O (30 mg, 0.20 mmol), and 2-aminonicotinic acid methyl ester (269 mg, 1.77 mmol) were heated at 160° C. in hexanol (5 mL) for 12 hours. Upon cooling, the mixture was purified via flash chromatography CH2Cl2/MeOH (95:5), followed by a second flash column eluting with Et2OAc/hexanes (7:3) to provide 11 mg (2%) of the product. 1H NMR (CDCl3, 400 MHz) δ: 13.5 (s, 1H), 8.80 (br s, 1H), 8.62 (d, 1H), 7.25 (dd, 1H), 6.22 (d, 1H), 6.04 (s, 1H), 5:97 (s, 1H), 3.86-3.83 (m, 4H), 3.40-3.35 (m, 4H). LRMS (APCI, positive): Da/e 296.4 (m−1).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was purified via flash chromatography CH2Cl2/MeOH (95:5)
  3. washeluting with Et2OAc/hexanes (7:3)

Sources & evidence

ORD record
ord-45ad2f8dac534f37b59170332cc0e9fb
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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