3-Amino-4-hydroxypyridine → 2-(3-Methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[4,5-c]pyridine

HRID 7778

반응식

HRID 7778 반응식
C[Si](OP(=O)=O)(C)C.[NH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[OH:16].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:22](O)=O>>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:22]2[O:16][C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:9]=2)[CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

참가 물질

4

반응물 3

HCID 2333923-Amino-4-hydroxypyridineHCID 16133246Trimethyl(phosphooxy)silaneHCID 219565153-Methoxy-4-(pyridin-2-yl)benzoic acid

생성물 1

HCID 102863392-(3-Methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[4,5-c]pyridine

반응 조건

온도
200 °C

실험 절차

To 7 mL trimethylsilyl polyphosphate was added 3-aminopyridin-4-ol (330 mg, 3.00 mmol) and 3-methoxy-4-pyridin-2-ylbenzoic acid (460 mg, 2.00 mmol). The mixture was heated at 200° C. for 2 h, quenched over ice, and made basic (pH 14) with 1N NaOH. The aqueous phase was extracted with MTBE (3×200 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (50–100% EtOAc/hexanes followed by 10% MeOH/CHCl3) to give 2-(3-Methoxy-4-pyridin-2-ylphenyl)[1,3]oxazolo[4,5-c]pyridine as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 9.16 (s, 1H), 8.71 (d, 1H), 8.62 (d, 1H), 8.03–7.84 (m, 6H), 7.39 (t, 1H), 4.00 (s, 3H); MS (ESI) 304 (M+H)+.

후처리

  1. customquenched over ice
  2. extractionThe aqueous phase was extracted with MTBE (3×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (50–100% EtOAc/hexanes followed by 10% MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-66bdbd2e29424c5a85410be355427813
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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