Tetrahydrofuran → HCID 178520269, 화합물

HRID 45846

반응식

HRID 45846 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.O1CCCC1.ON1C2C=CC=CC=2N=N1.[F:30][C:31]1[C:36]([C:37]2[C:41]([C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)=[CH:40][NH:39][N:38]=2)=[C:35]([F:48])[CH:34]=[CH:33][C:32]=1[NH2:49]>>[F:30][C:31]1[C:36]([C:37]2[C:41]([C:42]3[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=3)=[CH:40][NH:39][N:38]=2)=[C:35]([F:48])[CH:34]=[CH:33][C:32]=1[NH:49][C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:13])=[CH:8][CH:7]=1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 178507659HCID 178507659, 화합물

생성물 1

HCID 178520269HCID 178520269, 화합물

실험 절차

To (4-trifluoromethyl-phenyl)-acetic acid (49 mg, 0.24 mmol) in anhydrous tetrahydrofuran (3 mL) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (63 mg, 0.24 mmol) was added, after 10 minutes 1-hydroxybenzotriazole (38 mg, 0.28 mmol) and after 30 minutes 2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (60 mg, 0.22 mmol) (prepared as described in Example 22) were added. The reaction was stirred under nitrogen atmosphere at room temperature overnight to yield a mixture of mono- and bis-amide (3:1 ratio at 254 nm). The reaction was concentrated under reduced pressure and the residue was dissolved in ethyl acetate, washed successively with NaHCO3 saturated solution and the organic layer was dried over anhydrous sodium sulfate and filtered. The monoamide derivative was isolated by silica gel column chromatography eluting with ethanol 7% in methylene chloride.

후처리

  1. customto yield
  2. concentrationThe reaction was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed successively with NaHCO3 saturated solution
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe monoamide derivative was isolated by silica gel column chromatography
  8. washeluting with ethanol 7% in methylene chloride

출처 및 근거

ORD 기록
ord-38614a09dc6d4eafb4a8bf46d710531a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541575B2

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