Dimethylamine, hydrochloride → HCID 54315398, compound

HRID 1604667Notes

Reaction equation

HRID 1604667 reaction equation
[CH2:1]([N:3]=[C:4]=NCCCN(C)C)C.[C:12]([C:16]1[N:17]=[C:18]([C:21]2[O:22][C:23]3[CH:29]=[CH:28][C:27]([CH2:30][N:31]4[C:39]5[C:34](=[CH:35][C:36]([O:40][CH2:41][C:42]([OH:44])=O)=[CH:37][CH:38]=5)[C:33]([CH2:45][C:46]([O:48][CH3:49])=[O:47])=[CH:32]4)=[CH:26][C:24]=3[CH:25]=2)[S:19][CH:20]=1)([CH3:15])([CH3:14])[CH3:13].Cl.CNC>ClCCl>[C:12]([C:16]1[N:17]=[C:18]([C:21]2[O:22][C:23]3[CH:29]=[CH:28][C:27]([CH2:30][N:31]4[C:39]5[C:34](=[CH:35][C:36]([O:40][CH2:41][C:42](=[O:44])[N:3]([CH3:4])[CH3:1])=[CH:37][CH:38]=5)[C:33]([CH2:45][C:46]([O:48][CH3:49])=[O:47])=[CH:32]4)=[CH:26][C:24]=3[CH:25]=2)[S:19][CH:20]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 54304027HCID 54304027, compound

Product 1

HCID 54315398HCID 54315398, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide (46.5 mg) was added to a mixture of methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(carboxymethoxy)indole-3-acetate (145 mg), dimethylamine hydrochloride (24.4 mg) and 1H-hydroxybenzotriazole hydrate (40.4 mg) in dichloromethane (2 ml) and then the mixture was stirred at room temperature for 2 hours. After removal of solvent, the residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(N,N-dimethylcarbamoylmethoxy)-indole-3-acetate (0.16 g).

Workup

  1. customAfter removal of solvent
  2. customthe residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixture of n-hexane and ethyl acetate
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-098409e6ad0b4d748542c873c07d3f3c
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

Loading…