Sodium Methoxide → (S)-7-bromo-3-chloro-1-methoxy-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

HRID 335965노트

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HRID 335965 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12]([Cl:21])[N:11]=[C:10](F)[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[CH3:23][O-:24].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C@@:15]3([CH2:19][O:18][C:17]([NH2:20])=[N:16]3)[C:14]3[CH:13]=[C:12]([Cl:21])[N:11]=[C:10]([O:24][CH3:23])[C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 58466258(S)-7-bromo-3-chloro-1-fluoro-5'H-spiro[chromeno[2,3-c]pyridine-5,4' oxazol]-2'-amine

생성물 1

HCID 58466132(S)-7-bromo-3-chloro-1-methoxy-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

시약·촉매·용매 1

HCID 887Methanol용매

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온도
65 °C

실험 절차

A 100 mL RBF containing a solution of (S)-7-bromo-3-chloro-1-fluoro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.50 g, 1.30 mmol, prepared as described in Method BB33) in methanol (13 mL) was treated with sodium methoxide (0.36 mL, 6.50 mmol) and the resulting suspension was heated to 65° C. for 3 h on a hot-plate. The reaction was cooled to RT and concentrated to dryness under high vacuum. The resulting yellowish residue was taken up in dichloromethane (75 mL), water (25 mL), and the organic layer was separated. The organic layer was dried over sodium sulfate and concentrated to yield the crude product. The crude product was purified by silica gel flash column chromatography and eluted using DCM/MeOH gradient to provide (S)-7-bromo-3-chloro-1-methoxy-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as an amorphous off-white solid. [MS: m/z=395.9 (M+H)].

후처리

  1. temperatureThe reaction was cooled to RT
  2. concentrationconcentrated to dryness under high vacuum
  3. customwater (25 mL), and the organic layer was separated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto yield the crude product
  7. customThe crude product was purified by silica gel flash column chromatography
  8. washeluted

출처 및 근거

ORD 기록
ord-8962f13fae884e4ab242f69370a5f216
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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