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 1070702ノート

反応式

HRID 1070702 の反応式
[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

参加物

7

反応物 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

生成物 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-pentadienamide収率 73%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-527d9aa0fc16496688d8b01b8c06a3af
出典データセット
uspto-grants-2005_06
特許番号
US06903117B2

反応ノート

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