N,N-Dimethylglycine → HCID 22479181, compound

HRID 2182605Notes

Reaction equation

HRID 2182605 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=4)[C:13](=[O:25])[N:12]2[CH2:11][CH2:10][NH:9][CH2:8]3)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:47][N:48]([CH3:53])[CH2:49][C:50](O)=[O:51]>C1COCC1.C(Cl)CCl>[CH3:47][N:48]([CH2:49][C:50]([N:9]1[CH2:8][C:7]2([CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Br:1])=[CH:3][CH:4]=3)[N:12]([C:13](=[O:25])[N:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:15]2=[O:16])[CH2:11][CH2:10]1)=[O:51])[CH3:53]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22479108HCID 22479108, compound

Product 1

HCID 22479181HCID 22479181, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-bromobenzyl)-8-(3,5-dichlorophenyl)-1,4,8-triazabicyclo[4.3.0]nonane-7,9-dione (0.085 g) in THF (5 mL) was added DIEA (0.1 mL), HOBt (0.57 g), EDC (0.054 g) and N,N-dimethylglycine (0.037 g). After stirring overnight, the reaction was concentrated and the residue was diluted with EtOAc and washed with water, NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (Silica gel: 2% MeOH/CH2Cl2, Chromatotron) afforded the titled compound. (0.093 g). MS (m/z) 553 (MH+). mp 73.5° C.

Workup

  1. concentrationthe reaction was concentrated
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water, NaHCO3, and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (Silica gel: 2% MeOH/CH2Cl2, Chromatotron)

Sources & evidence

ORD record
ord-d61331196d3e4d6e9770ece68530e5d1
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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