1-Hydroxybenzotriazole → (2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[(2-{4-[(3,5-dichloro-2-pyridyl)oxy]-1-piperidinyl}-2-oxoethyl)amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamide

HRID 1246756노트

반응식

HRID 1246756 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:14]([NH:16][CH2:17][C:18]([OH:20])=O)=[O:15])=[O:11])=[CH:4][CH:3]=1.Cl.Cl.[Cl:30][C:31]1[C:32]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[N:33][CH:34]=[C:35]([Cl:37])[CH:36]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:14]([NH:16][CH2:17][C:18]([N:42]2[CH2:43][CH2:44][CH:39]([O:38][C:32]3[C:31]([Cl:30])=[CH:36][C:35]([Cl:37])=[CH:34][N:33]=3)[CH2:40][CH2:41]2)=[O:20])=[O:15])=[O:11])=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219060913,5-Dichloro-2-(4-piperidinyloxy)pyridine dihydrochlorideHCID 69379045[[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acid

생성물 1

HCID 69379614(2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[(2-{4-[(3,5-dichloro-2-pyridyl)oxy]-1-piperidinyl}-2-oxoethyl)amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamide수율 76.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of {[(2S)-2-{[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino}-3-(2-pyridyl)propanoyl]amino}acetic acid (0.19 g), 3,5-dichloro-2-(4-piperidinyloxy)pyridine dihydrochloride (0.16 g), 1-hydroxybenzotriazole (0.084 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g) in N,N-dimethylformamide (2.5 ml) was added dropwise N,N-diisopropylethylamine (0.27 ml) at 8° C. The mixture was warmed to room temperature and stirred for 6 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the title compound (231 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ea858edac1a64b4083b1cfca2779459a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129243B2

반응 노트

불러오는 중…