Water → 5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]-N-(pyridin-4-ylmethyl)oxazol-2-amine

HRID 1854605Notes

Reaction equation

HRID 1854605 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.O>CC(O)C>[CH3:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:11]2[N:12]=[C:7]([C:4]3[O:3][C:2]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)=[N:6][CH:5]=3)[CH:8]=[CH:9][CH:10]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 773174-PyridinemethanamineHCID 53311311HCID 53311311, compound

Product 1

HCID 673458655-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]-N-(pyridin-4-ylmethyl)oxazol-2-amineYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (50 mg, 0.174 mmol) in iPrOH (5 ml) was treated with 4-aminomethylpyridine (53 μl) and heated to reflux for 40 h. The cooled mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on Al2O3 (Brockman grade III, 7% H2O), eluting with 2% EtOH in DCM. Precipitation from DCM with n-pentane afforded the title compound as pale yellow solid (34 mg, 55%). 1H NMR (300 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.52 (d, J=4.6 Hz, 2H), 8.25 (t, J=5.8 Hz, 1H), 8.08 (d, J=5.0 Hz, 1H), 7.73 (s, 1H), 7.64 (t, J=7.9 Hz, 1H), 7.47 (d, J=8.3 Hz, 1H), 7.36 (d, J=4.9 Hz, 2H), 7.29 (s, 1H), 6.92 (d, J=7.6 Hz, 1H), 6.73 (d, J=5.0 Hz, 1H), 4.49 (d, J=5.7 Hz, 2H), 2.29 (s, 3H). (ESI+) m/z 359 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 40 h
  3. extractionextracted with DCM
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure before purification by column chromatography on Al2O3 (Brockman grade III, 7% H2O)
  7. washeluting with 2% EtOH in DCM
  8. customPrecipitation from DCM with n-pentane

Sources & evidence

ORD record
ord-2489bbc078634981adf6341de5cf05e3
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

Loading…