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

HRID 2065050ノート

反応式

HRID 2065050 の反応式
N#N.[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14][N:15]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]3)=[N:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[S:13][C:12]([CH2:14][N:15]3[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]3)=[N:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1

参加物

7

反応物 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 66928948HCID 66928948、化合物

生成物 1

HCID 669288311-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-1H-pyrazol-4-ylamine

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(2-methyl-[1,3]dioxolan-2-yl)-2-(4-nitro-pyrazol-1-ylmethyl)-thiazole (490 mg, 1.65 mmol), iron powder (280 mg, 4.96 mmol) and NH4Cl (447 mg, 8.27 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 brown oil. TLC: rf (19:1 CH2Cl2-MeOH)=0.20. LC-MS-conditions 02: tR=0.56 min; [M+H]+=267.29.

後処理

  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

出典と根拠

ORDレコード
ord-3af9ff6ee4584fe79d4126a3bac3c3bd
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

反応ノート

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