4-Amino-1,2,2,6,6-pentamethylpiperidine → (2Z,4E)-5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-N-(1,2,2,6,6-pentamethyl piperidin-4-yl)-2,4-pentadienamide

HRID 1070702노트

반응식

HRID 1070702 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](/[CH:12]=[CH:13]/[CH:14]=[C:15](\[O:19][CH3:20])/[C:16]([OH:18])=O)=[CH:5]2.[NH2:21][CH:22]1[CH2:27][C:26]([CH3:29])([CH3:28])[N:25]([CH3:30])[C:24]([CH3:32])([CH3:31])[CH2:23]1.O.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](/[CH:12]=[CH:13]/[CH:14]=[C:15](\[O:19][CH3:20])/[C:16]([NH:21][CH:22]1[CH2:23][C:24]([CH3:31])([CH3:32])[N:25]([CH3:30])[C:26]([CH3:29])([CH3:28])[CH2:27]1)=[O:18])=[CH:5]2

참가 물질

7

반응물 4

HCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219174661-Hydroxy-7-azabenzotriazol hydrateHCID 22397576(2Z,4E)-5-(5,6-dichloro-1H-indol-2-yl)-2-methoxy-2,4-pentadienoic acid

생성물 1

HCID 9890618(2Z,4E)-5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-N-(1,2,2,6,6-pentamethyl piperidin-4-yl)-2,4-pentadienamide수율 73%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of (2Z,4E)-5-(5,6-dichloro-1H-indol-2-yl)-2-methoxy-2,4-pentadienoic acid (736 mg, 3.65 mmol), 4-amino-1,2,2,6,6-pentamethylpiperidine (620 mg, 3.65 mmol), 1-hydroxy-7-azabenzotriazole hydrate (474.5 mg, 3.65 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (693.5 mg, 3.65 mmol) in DMF (2 ml) was stirred at RT overnight. The solution was poured into brine (20 ml) and repeatedly extracted with EtOAc. The organic phase was washed with 5% aq. CaCO3, dried (MgSO4) and evaporated under vacuum. The residue was chromatographed on silica gel using ethyl acetate:methanol:aq. ammonia (32%) 90:10:2 as eluent mixture. The collected fractions produced the pure title compound (0.8, yield 73%) as yellow crystals, m.p.=212° C.

후처리

  1. extractionrepeatedly extracted with EtOAc
  2. washThe organic phase was washed with 5% aq. CaCO3
  3. dry with materialdried (MgSO4)
  4. customevaporated under vacuum
  5. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-527d9aa0fc16496688d8b01b8c06a3af
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903117B2

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