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

HRID 2065039ノート

反応式

HRID 2065039 の反応式
N#N.[CH3:3][C:4]1([C:9]2[S:10][CH:11]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[N:16]3)[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][CH:11]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][C:17]([NH2:20])=[N:16]3)[N:13]=2)[O:8][CH2:7][CH2:6][O:5]1

参加物

7

反応物 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 669292022-(2-Methyl-[1,3]dioxolan-2-yl)-4-(3-nitro-pyrazol-1-ylmethyl)-thiazole

生成物 1

HCID 669286501-[2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-4-ylmethyl]-1H-pyrazol-3-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
85 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a 0.1M solution of 2-(2-methyl-[1,3]dioxolan-2-yl)-4-(3-nitro-pyrazol-1-ylmethyl)-thiazole (160 mg, 0.54 mmol), iron powder (91 mg, 1.62 mmol) and NH4Cl (146 mg, 2.70 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 85° C. for 30 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 an oil. LC-MS-conditions 02: tR=0.60 min; [M+H]+=267.30.

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-e2b992bfbc41446297e550114937362b
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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