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

HRID 460260노트

반응식

HRID 460260 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c7ac41fef324358b8bd4167e5949d5b
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196104B2

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