Nitrogen → 1-[2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-5-ylmethyl]-1H-pyrazol-4-ylamine

HRID 2065054

반응식

HRID 2065054 반응식
N#N.[CH3:3][C:4]1([C:9]2[S:10][C:11]([CH2:14][N:15]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]3)=[CH:12][N:13]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[S:10][C:11]([CH2:14][N:15]3[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]3)=[CH:12][N:13]=2)[O:8][CH2:7][CH2:6][O:5]1

참가 물질

7

반응물 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 669287342-(2-Methyl-[1,3]dioxolan-2-yl)-5-(4-nitro-pyrazol-1-ylmethyl)-thiazole

생성물 1

HCID 669293321-[2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-5-ylmethyl]-1H-pyrazol-4-ylamine

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(2-methyl-[1,3]dioxolan-2-yl)-5-(4-nitro-pyrazol-1-ylmethyl)-thiazole (460 mg, 1.55 mmol), iron powder (263 mg, 4.66 mmol) and NH4Cl (419 mg, 7.76 mmol) in a mixture of EtOH (3.0 mL) and water (1.5 mL) was stirred at 75° C. for 60 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (10 mL) was added followed by 1N NaOH (10 mL). The aq. layer was extracted with CH2Cl2 (2×10 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a red oil. TLC: rf (19:1 CH2Cl2-MeOH)=0.20. LC-MS-conditions 02: tR=0.54 min; [M+H]+=266.93.

후처리

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated under reduced pressure
  3. additionCH2Cl2 (10 mL) was added
  4. extractionThe aq. layer was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

출처 및 근거

ORD 기록
ord-876a5fa3efaf4ed1b3c2ff31e9e73834
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288419B2

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