Ethyl isocyanate → HCID 86731754, compound

HRID 1504882Notes

Reaction equation

HRID 1504882 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C:9]1[CH:10]=[C:11]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[N:20]=2)[C:12]([C:15]([NH2:17])=[O:16])=[N:13][CH:14]=1.[CH2:27]([N:29]=[C:30]=[O:31])[CH3:28].C(N(CC)CC)C>C1COCC1>[CH3:25][C:23]1[CH:22]=[C:21]([CH3:26])[N:20]=[C:19]([NH:18][C:11]2[C:12]([C:15]([NH2:17])=[O:16])=[N:13][CH:14]=[C:9]([NH:8][C:30](=[O:31])[NH:29][CH2:27][CH3:28])[CH:10]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 8471Triethylamine2×HCID 86731755HCID 86731755, compound

Product 1

HCID 86731754HCID 86731754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt (50 mg, 0.13 mmol) in THF (1 mL) was added ethyl isocyanate (12 mg, 0.18 mmol) and triethylamine (0.075 mL, 0.54 mmol), and the reaction mixture was stirred for 2 hours at room temperature. Additional ethyl isocyanate (12 mg, 0.18 mmol) and triethylamine (0.075 mL, 0.54 mmol) were added, and the reaction mixture was heated to 55° C. for 18 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to afford 3-[(4,6-dimethylpyridin-2-yl)amino]-5-[(ethylcarbamoyl)amino]pyridine-2-carboxamide. MS ESI calc'd. for C16H21N6O2 [M+H]+ 329. found 329. 1H NMR (500 MHz, DMSO-d6) δ 11.61 (s, 1H), 9.24 (s, 1H), 8.86 (s, 1H), 8.23 (d, J=2.2 Hz, 1H), 8.13 (s, 1H), 7.57 (s, 1H), 6.63 (s, 1H), 6.53 (s, 1H), 6.33 (t, J=5.3 Hz, 1H), 3.20-3.07 (m, 2H), 2.40 (s, 3H), 2.23 (s, 3H), 1.06 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturethe reaction mixture was heated to 55° C. for 18 hours
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)

Sources & evidence

ORD record
ord-58c4e83bef2546caa50e73f7b277de90
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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