Tetrahydrofuran → 1-(3-Hydroxy-pyridin-2-yl)-3-(2-pyridin-3-yl-thiazol-4-yl)-urea

HRID 479707Notes

Reaction equation

HRID 479707 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][CH:9]=[C:10](C(O)=O)[N:11]=2)[CH:2]=1.P([N:31]=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[NH2:34][C:35]1C=CC=[C:37]([OH:41])[N:36]=1.[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>>[OH:45][C:46]1[C:35]([NH:36][C:37]([NH:31][C:10]2[N:11]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[S:8][CH:9]=2)=[O:41])=[N:34][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 123414Diphenylphosphoryl azideHCID 7365132-(3-Pyridyl)thiazole-4-carboxylic acidHCID 1785076342-Amino-6-hydroxypyridine

Product 1

HCID 187716021-(3-Hydroxy-pyridin-2-yl)-3-(2-pyridin-3-yl-thiazol-4-yl)-urea

Procedure

TEA (0.27 mL, 1.94 mmol) was added to a solution of 2-(pyridin-3-yl)thiazole-4-carboxylic acid (200 mg, 0.97 mmol) and 4A molecular sieves in THF (25 mL) under N2 at RT. (PhO)2PON3 (0.33 mL, 1.55 mmol) followed by 2-amino-6-hydroxypyridine (268 mg, 2.43 mmol) was added and the resulting mixture heated at reflux for 12 h. After cooling to RT, the heterogeneous mixture was decanted to remove the molecular sieves. The precipitate was collected, rinsing with EtOAc to give a white solid. MS m/z: 313.0 (M+H). Calc'd for C14H11N5O2S-313.34.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture heated
  3. temperatureat reflux for 12 h
  4. customthe heterogeneous mixture was decanted
  5. customto remove the molecular sieves
  6. customThe precipitate was collected
  7. washrinsing with EtOAc
  8. customto give a white solid

Sources & evidence

ORD record
ord-a96d9c73730c4d79a488f2b8a0713ebf
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

Loading…