Bay-H-1127 → ethyl 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetate

HRID 2225208노트

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HRID 2225208 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[NH2:12].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=O.C([BH3-])#N.[Na+]>CC(O)=O.CO.C1(C)C=CC=CC=1>[F:14][C:2]([F:1])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[NH:12][CH2:16][C:15]([O:19][CH2:20][CH3:21])=[O:18]

참가 물질

6

반응물 3

HCID 16736Bay-H-1127HCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 68469013ethyl 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 10129899Acetic acid methanol용매

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온도
100 °C

실험 절차

Preparation I6, Step 2: A solution of 5-(trifluoromethyl)-1H-indazol-3-amine (2.08 g, 10.3 mmol) in 50 mL of 1% AcOH/MeOH was charged with ethyl glyoxylate (2.05 mL of a 50% solution in toluene, 10.3 mmol; note: the commercially available material is polymeric and was heated at 100° C. for 90 min before being used immediately in this reaction) and sodium cyanoborohydride (777 mg, 12.4 mmol). The mixture was stirred for 2.5 h, quenched with sat. NaHCO3, and extracted with EtOAc (2×). The organic extracts were combined, washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification by flash chromatography provided ethyl 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetate (819 mg).

후처리

  1. customPreparation I6, Step 2
  2. customquenched with sat. NaHCO3
  3. extractionextracted with EtOAc (2×)
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-6ea550606c864c1a877d8a687fbdf8ce
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378409B2

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