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

HRID 479707ノート

反応式

HRID 479707 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a96d9c73730c4d79a488f2b8a0713ebf
出典データセット
uspto-grants-2003_11
特許番号
US06645990B2

反応ノート

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