1-Hydroxybenzotriazole → 1-(3-(3,4-Dimethoxyphenethyl)-2-oxo-3,10-diazabicyclo[4.3.1]-decan-10-yl)-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione

HRID 2205591Notes

Reaction equation

HRID 2205591 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][CH2:7][N:8]1[CH2:16][CH2:15][CH:14]2[NH:17][CH:10]([CH2:11][CH2:12][CH2:13]2)[C:9]1=[O:18].[O:24]=[C:25]([C:29]1[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=1)[C:26](O)=[O:27].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:6][CH2:7][N:8]1[CH2:16][CH2:15][CH:14]2[N:17]([C:26](=[O:27])[C:25]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)=[O:24])[CH:10]([CH2:11][CH2:12][CH2:13]2)[C:9]1=[O:18]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111283972-oxo-2-(3,4,5-trimethoxyphenyl)acetic AcidHCID 899399413-(3,4-Dimethoxyphenethyl)-3,10-diazabicyclo[4.3.1]decan-2-one

Product 1

HCID 781433951-(3-(3,4-Dimethoxyphenethyl)-2-oxo-3,10-diazabicyclo[4.3.1]-decan-10-yl)-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3,4-dimethoxyphenethyl)-3,10-diazabicyclo[4.3.1]decan-2-one (27 mg, 0.09 mmol) in 3 ml DCM was added sequentially 2-oxo-2-(3,4,5-trimethoxyphenyl) acetic acid (23 mg, 0.1 mmol), EDC-HCl (20 mg, 0.1 mmol), HOBt (14 mg, 0.1 mmol), TEA (10 mg, 0.1 mmol) at room temperature and stirred overnight. The reaction was quenched with saturated NH4Cl solution (5 ml), extracted with DCM (4×10 ml). The organic layers were dried over MgSO4 and concentrated in vacuo. The reaction mixture was purified with flash chromatography in EtOAc. TLC [EtOAc]: Rf=0.42

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution (5 ml)
  2. extractionextracted with DCM (4×10 ml)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe reaction mixture was purified with flash chromatography in EtOAc

Sources & evidence

ORD record
ord-52d45968e6114ea28fc50e279d5660d0
Source dataset
uspto-grants-2016_06
Patent number
US09371322B2

Reaction notes

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