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, 화합물

HRID 1481539

반응식

HRID 1481539 반응식
[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]

참가 물질

4

반응물 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

생성물 1

HCID 178494020HCID 178494020, 화합물

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-89fe2f4773af41c7a134929bf57a8b17
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409915B2

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