Water → 6-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

HRID 346691

반응식

HRID 346691 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15](Cl)[N:14]=[C:13]([Cl:18])[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:19]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.O.[OH-].[Na+]>CC(C)=O.C(OCC)(=O)C>[Cl:18][C:13]1[N:12]=[C:11]([NH:10][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[N:16]=[C:15]([NH:26][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:14]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 2899CycloheptylamineHCID 14798Sodium HydroxideHCID 21896921(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

생성물 1

HCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine수율 70.5%

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a sample of compound 101 (20.02 g, 65.6 mmol) in acetone (200 mL) was added cycloheptylamine (8.3 mL, 65.5 mmol) in acetone (55 mL) slowly by addition funnel at rt. Then water (66 mL) was added followed by aqueous sodium hydroxide (26.2 mL, 2.5 N, 65.5 mmol) by addition funnel. The reaction mixture was heated at reflux under a nitrogen atmosphere for approximately about 3 hours. The reaction was cooled, diluted with ethyl acetate, washed 1 time with water, and finally 1 time with brine. The organic layer was separated and dried over potassium carbonate/sodium sulfate. The organic layer was filtered and concentrated in vacuo. The product (24.13 g) was purified by flash column chromatography (silica gel, 1:4 ethyl acetate: hexanes). The fractions were combined and concentrated in vacuo to afford 133 as a pale yellow solid (17.66 g, 70.5%), mp 146° C.; HPLC: Inertsil ODS-3V C18, 40:10:50 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 58.8 min, 99.9% purity); MS (ESI): m/z 382 (M+H, 100), 241 (2.8), 226 (8.4), 139 (43.5), 116 (6).

후처리

  1. additionslowly by addition funnel at rt
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux under a nitrogen atmosphere for approximately about 3 hours
  4. temperatureThe reaction was cooled
  5. washwashed 1 time with water, and finally 1 time with brine
  6. customThe organic layer was separated
  7. dry with materialdried over potassium carbonate/sodium sulfate
  8. filtrationThe organic layer was filtered
  9. concentrationconcentrated in vacuo
  10. customThe product (24.13 g) was purified by flash column chromatography (silica gel, 1:4 ethyl acetate: hexanes)
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fc2bf8fdb57642bd908f3ac8e167feee
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173032B2

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