1-Hydroxybenzotriazole → 1-Phenyl-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177974노트

반응식

HRID 1177974 반응식
CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[NH2:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]1)=[O:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:61]1([N:67]2[CH2:72][CH2:71][CH:70]([C:73](O)=[O:74])[CH2:69][CH2:68]2)[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C=O)C.O>[O:20]=[C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]1)[CH2:18][NH:17][C:73]([CH:70]1[CH2:69][CH2:68][N:67]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH2:72][CH2:71]1)=[O:74]

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 30239901-Phenylpiperidine-4-carboxylic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

생성물 1

HCID 251649261-Phenyl-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide수율 29.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (66 mg, 0.51 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt (125 mg, 0.29 mmol) in DMF (1.5 mL). HOBT (27 mg, 0.20 mmol) and EDCI.HCl (39 mg, 0.20 mmol) were then added at room temperature. After 2 minutes, 1-phenyl-piperidine-4-carboxylic acid (35 mg, 0.17 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 25 mg (29% yield) of 1-phenyl-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity %: 87.4%, 1H NMR (DMSO-d6): δ 7.8-7.7 (m, 3H), 7.4-7.3 (d, 1H), 7.3-7.2 (t, 1H), 7.0-6.9 (d, 1H), 6.8 (t, 1H), 6.6 (m, 1H), 4.2-3.8 (m, 4H), 3.8-3.6 (m, 4H), 3.5 (m, 2H), 3.4-3.3 (t, 1H), 3.2 (m, 2H), 2.7 (m, 2H), 2.3 (m, 1H), 2.0-1.8 (m, 4H).

후처리

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fbb646efef06400fa3d0fce7070b918b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

반응 노트

불러오는 중…