Ammonia → HCID 70921718, 화합물

HRID 2069134노트

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HRID 2069134 반응식
[CH3:1][C:2]1[C:15]([CH3:16])=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33].N>C1COCC1.CO>[CH3:1][C:2]1[C:15]([CH3:16])=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:32](=[O:33])[CH2:31][O:30][CH3:29])[CH:6]=1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 585648204-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine

생성물 1

HCID 70921718HCID 70921718, 화합물수율 67%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 4-(2,3-dimethyl-4-nitrophenoxy)pyridin-2-amine (110 mg, 0.424 mmol) in THF (3.0 mL) containing DIPEA (370 μL, 2.12 mmol) at 0° C. was added 2-methoxyacetyl chloride (155 μL, 1.70 mmol) in a single portion. The reaction mixture was warmed to RT for 1 hr and a solution of NH3 in MeOH (7M, 2.0 mL) was added and the resulting mixture maintained at RT for 16 hr and then evaporated in vacuo. The residue was partitioned between DCM (50 mL) and brine (40 mL) and the organic phase was seprated and dried (MgSO4) and was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 20-50% EtOAc in isohexane, gradient elution) to afford N-(4-(2,3-dimethyl-4-nitrophenoxy)pyridin-2-yl)-2-methoxyacetamide (94 mg, 67%) as an orange oil; Rt 2.14 min (Method 2); m/z 332 (M+H)+ (ES+).

후처리

  1. temperaturethe resulting mixture maintained at RT for 16 hr
  2. customevaporated in vacuo
  3. customThe residue was partitioned between DCM (50 mL) and brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customwas evaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 40 g, 20-50% EtOAc in isohexane, gradient elution)

출처 및 근거

ORD 기록
ord-aed2d25226024b81a063ca8fd3341b73
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299074B2

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