3-(2-Thienyl)-5-isoxazolamine → Ethyl 6-(5-methylpyridin-3-yl)-3-(thiophen-2-yl)isoxazolo[5,4-b]pyridine-4-carboxylate

HRID 595044

반응식

HRID 595044 반응식
O/[C:2](=[CH:8]\[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH3:17])[CH:16]=1)=O)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:27]=[C:26]([NH2:28])[O:25][N:24]=1>C(O)(=O)C>[CH3:17][C:15]1[CH:16]=[C:11]([C:9]2[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:27]3[C:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)=[N:24][O:25][C:26]=3[N:28]=2)[CH:12]=[N:13][CH:14]=1

참가 물질

4

반응물 2

HCID 2169013-(2-Thienyl)-5-isoxazolamineHCID 178473093HCID 178473093, 화합물

생성물 1

HCID 117844821Ethyl 6-(5-methylpyridin-3-yl)-3-(thiophen-2-yl)isoxazolo[5,4-b]pyridine-4-carboxylate

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 1-3 (150 mg, 0.638 mmol) and 1-4 (106 mg, 0.638 mmol) in acetic acid (3 mL) was heated at reflux for 3 h. The mixture was cooled to rt and concentrated. The residue was purified by column chromatography (0-100% EtOAc in hexane) to give 1-5 as a white solid: 1H NMR (400 MHz, CDCl3) δ 9.16 (s, 1H), 8.59 (s, 1H), 8.36 (s, 1H), 8.15 (s, 1H), 7.58 (m, 1H), 7.39 (m, 1H), 7.22 (m, 1H), 4.21 (q, J=7.2 Hz, 2H), 2.48 (s, 3H), 1.07 (t, J=7.2 Hz, 3H); ESI+ MS [M+H]+ C19H16N3O3S=366.0.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (0-100% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-bde9b82a95d14c6ab68c8973497111c4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242995B2

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