Dimethylamine → HCID 57461321, compound

HRID 1866804Notes

Reaction equation

HRID 1866804 reaction equation
[CH:1]1([N:7]=[C:8]=NC2CCCCC2)CCCCC1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][C:33]([OH:35])=O)=[CH:17]1.CNC>CN(C=O)C.C(#N)C>[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][C:33]([N:7]([CH3:8])[CH3:1])=[O:35])=[CH:17]1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 10850547HCID 10850547, compound

Product 1

HCID 57461321HCID 57461321, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

N,N′-Dicyclohexylcarbodiimide (875 mg, 4.2 mmol) is added to [2-(1H-Indol-3-ylsulfanyl)-phenyl]-acetic acid (600 mg, 2.1 mmol) in 3 mL dry DMF and 7 mL acetonitril and stirred for 10 minutes at room temperature. 5.3 mL dimethyl amine (2M in THF, 10.6 mmol) is added and the reaction mixture is stirred 16 hours at room temperature. The reaction mixture is concentrated in vacuo. The residue is extracted with ethyl acetate (3 times). The combined orgnic phases are washed with brine, dried with MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate/heptane) gives 116 mg (18%) of the title compound.

Workup

  1. stirringthe reaction mixture is stirred 16 hours at room temperature
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. extractionThe residue is extracted with ethyl acetate (3 times)
  4. washThe combined orgnic phases are washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-f5e09a4f3818452386a0d72b9229d4cb
Source dataset
uspto-grants-2009_12
Patent number
US07629473B2

Reaction notes

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