Hydrochloric Acid → HCID 69671321, 화합물

HRID 1497581노트

반응식

HRID 1497581 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[N:16]2[CH:17]=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[CH:19]=[CH:20][C:15]2=[N:14][N:13]=1.[Cl:29][Sn]Cl.C([O-])([O-])=O.[Na+].[Na+].Cl>C(OCC)(=O)C.O>[ClH:29].[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([C:12]2[N:16]3[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)[CH:19]=[CH:20][C:15]3=[N:14][N:13]=2)=[C:3]([O:2][CH3:1])[CH:8]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 69670985HCID 69670985, 화합물

생성물 1

HCID 69671321HCID 69671321, 화합물수율 32.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

A mixture of 3-(2-methoxy-4-nitrophenyl)-6-(4-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (50 mg, 0.13 mmol) and SnCl2 (120 mg, 0.65 mmol) in ethyl acetate (25 mL) was heated to reflux for 6 h under Argon. The reaction mixture was cooled to room temperature and basified to pH=10 with saturated aqueous Na2CO3. The biphasic solution was separated and the aqueous layer was extracted with ethyl acetate (40 mL). The combined organic layers were washed with brine and concentrated. The residue was purified by flash column chromatography (petroleum ether:ethyl acetate=2:1 to 0:1) to give crude product as yellow oil. The oil was stirred in a solution of HCl in ethyl acetate (2M, 20 mL) at room temperature, and then was mixed with water (30 mL). The aqueous phase was washed with ethyl acetate (30 mL), basified with saturated aqueous Na2CO3 to pH>10 and extracted with ethyl acetate (30 mL). The organic phase was stirred with a solution of HCl in ethyl acetate (2M, 10 mL) at room temperature for 2 h and concentrated in vacuo to give the title compound as yellow solids (16 mg, 30% yield). 1H NMR (DMSO-d6): 8.32 (s, 1H), 8.19 (dd, J=9.6 and 1.2 Hz, 1H), 8.09 (d, J=9.6 Hz, 1H), 7.72 (d, J=8.7 Hz, 2H), 7.36 (d, J=8.4 Hz, 1H), 7.08 (d, J=8.7 Hz, 2H), 6.61 (d, J=1.5 Hz, 1H), 6.52 (dd, J=8.4 and 1.5 Hz, 1H), 3.82 (s, 3H), 3.79 (s, 3H). MS: m/z 347.1 [M+H+].

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 6 h under Argon
  3. customThe biphasic solution was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (40 mL)
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (petroleum ether:ethyl acetate=2:1 to 0:1)
  8. customto give crude product as yellow oil
  9. washThe aqueous phase was washed with ethyl acetate (30 mL)
  10. extractionextracted with ethyl acetate (30 mL)
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-88e4c3d2c153467baac4560b6b997e6a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199983B2

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