N-(2-amino-4-chloro-5-(trifluoromethyl)phenyl)-3-(3-oxocyclobutyl)propanamide → HCID 178515984, 화합물

HRID 2040644

반응식

HRID 2040644 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[NH:13][C:14](=O)[CH2:15][CH2:16][CH:17]1[CH2:20][C:19](=[O:21])[CH2:18]1>C(O)(=O)C>[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]2[N:13]=[C:14]([CH2:15][CH2:16][CH:17]3[CH2:20][C:19](=[O:21])[CH2:18]3)[NH:1][C:2]=2[CH:7]=1

참가 물질

3

반응물 1

HCID 67773908N-(2-amino-4-chloro-5-(trifluoromethyl)phenyl)-3-(3-oxocyclobutyl)propanamide

생성물 1

HCID 178515984HCID 178515984, 화합물수율 66.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
65 °C

실험 절차

N-(2-amino-4-chloro-5-(trifluoromethyl)phenyl)-3-(3-oxocyclobutyl)propanamide (72 mg, mmol) was taken up in acetic acid (3.2 mL) and the solution was heated at 65° C. for 26 h, upon which HPLC indicated the starting material was consumed and a new product had formed. The reaction mixture was cooled and the solvent was removed under high vac. The light brown residue was taken up in 20 mL ethyl acetate and the organic phase was washed with 10 mL portions of sat NaHCO3 and H2O. The organic phase was dried over Na2SO4, filtered and concentrated to yield a light brown glass. The crude material was purified by prep TLC (20 cm×20 cm×1.0 mm prep TLC plate, 3% MeOH/EA) to yield the title compound (45 mg, 66%) as a tan glass: MS (ESI+) for C14H12ClF3N2O m/z 317.2 (M+H)+; MS (ESI−) for C14H12ClF3N2O m/z 315.2 (M−H)−; HPLC purity 84.1% (ret. time, 2.98 min).

후처리

  1. customwas consumed
  2. customa new product had formed
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed under high vac
  5. washthe organic phase was washed with 10 mL portions of sat NaHCO3 and H2O
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a light brown glass
  10. customThe crude material was purified by prep TLC (20 cm×20 cm×1.0 mm prep TLC plate, 3% MeOH/EA)

출처 및 근거

ORD 기록
ord-bab0c6434066459fa65d3c11b049cc42
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580762B2

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