Trifluoroacetic acid → (S)-N-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide

HRID 1971098노트

반응식

HRID 1971098 반응식
[CH3:1][C:2]([CH3:36])([CH3:35])[C@H:3]([NH:10][C:11]([C:13]1[N:14]=[C:15]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:17]=12)=[O:12])[C:4]1[O:8][N:7]=[C:6]([CH3:9])[N:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]([CH3:36])([CH3:35])[C@H:3]([NH:10][C:11]([C:13]1[N:14]=[C:15]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][C:17]=12)=[O:12])[C:4]1[O:8][N:7]=[C:6]([CH3:9])[N:5]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 57635507(S)-tert-butyl 1-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propylcarbamoyl)-3-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate

생성물 1

HCID 57635129(S)-N-(2,2-dimethyl-1-(3-methyl-1,2,4-oxadiazol-5-yl)propyl)-3-phenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide수율 93.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Intermediate 22D (170 mg, 0.34 mmol) was dissolved in DCM (2 mL) and TFA (0.5 mL) was added. The resulting mixture was stirred for 2 h. The mixture was concentrated, neutralized with NaHCO3 saturated solution and extracted several times with EtOAc. The combined organic extracts were washed successively with water and brine, dried over anhydrous Na2SO4, filtered and concentrated to give of Compound 282 (125 mg, 87%). 1H-NMR (400 MHz, CDCl3-d) δ: 1.09 (s, 9H), 2.40 (s, 3H), 3.78 (m, 2H), 4.11 (m, 2H), 5.01 (m, 2H), 5.37 (d, 1H), 7.35 (m, 3H), 7.64 (m, 2H), 7.78 (d, 1H), LCMS (+ESI) m/z 395.0 [M+H]+.

후처리

  1. concentrationThe mixture was concentrated
  2. extractionextracted several times with EtOAc
  3. washThe combined organic extracts were washed successively with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2df2187f88534a7bbd6524593731b256
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431565B2

반응 노트

불러오는 중…