4-Amino-1,2,2,6,6-pentamethylpiperidine → HCID 9890618, compound

HRID 1070702Notes

Reaction equation

HRID 1070702 reaction equation
[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

Participants

7

Reactant 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

Product 1

HCID 9890618HCID 9890618, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-527d9aa0fc16496688d8b01b8c06a3af
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Reaction notes

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