5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [2-methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide → HCID 178494020、化合物

HRID 570219

反応式

HRID 570219 の反応式
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([NH:12][C:13]([C:15]2[N:16]([CH3:25])[N:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=2[Cl:20])=O)[CH:6]=[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]([F:35])([F:34])[F:33])[N:4]=1>CC(O)=O.[Fe]>[C:21]([C:18]1[C:19]([Cl:20])=[C:15]([C:13]2[NH:9][C:8]3[C:3]([O:2][CH3:1])=[N:4][C:5]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:35])([F:34])[F:33])=[CH:6][C:7]=3[N:12]=2)[N:16]([CH3:25])[N:17]=1)([CH3:24])([CH3:23])[CH3:22]

参加物

4

反応物 1

HCID 674116535-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [2-methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide

生成物 1

HCID 178494020HCID 178494020、化合物

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A solution of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [2-methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide (149 mg, 0.291 mmol, prepared as described in STEP A above) in AcOH (10 mL) was treated with iron powder (81.3 mg, 1.46 mmol), and the resulting mixture was heated to 100° C. for 1.5 h. The cooled mixture was concentrated in vacuo, taken up in saturated aqueous NaHCO3 (50 mL), and extracted twice with EtOAc (40 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 12-g SEPRA Si 50 SPE column (Flow rate=15 mL/min; Eluent=EtOAc-hexanes, 1:99 for 10 min, then 1:99 to 1:4 over 40 min) to yield 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine as a white solid. Mass Spectrum (LCMS, ESI pos.): Calculated for C22H21N5OClF3: 464.1 (M+H); Measured: 464.2.

後処理

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. extractionextracted twice with EtOAc (40 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a 12-g SEPRA Si 50 SPE column (Flow rate=15 mL/min

出典と根拠

ORDレコード
ord-09c701b3c3eb4fe9b7de4e4ca830865d
出典データセット
uspto-grants-2015_05
特許番号
US09023846B2

関連ノート

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