Dimethylamine, hydrochloride → HCID 11197576, compound

HRID 1694701Notes

Reaction equation

HRID 1694701 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[Cl:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])=[C:8]([C:21]2[CH:22]=[N:23][C:24](S(CCC)(=O)=O)=[N:25][CH:26]=2)[CH:7]=1.C(N(CC)C(C)C)(C)C>CCOC(C)=O>[Cl:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][C:12]([OH:14])=[O:13])=[C:8]([C:21]2[CH:26]=[N:25][C:24]([N:3]([CH3:4])[CH3:2])=[N:23][CH:22]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 86609216HCID 86609216, compound

Product 1

HCID 11197576HCID 11197576, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Dimethylamine hydrochloride (0.82 g) was added to a stirred solution of the product from step (iv) (0.2 g) and N,N-diisopropylethylamine (0.9 ml) in No (5 ml). The reaction mixture was heated at 90° C. for 6 h then diluted with EtOAc, washed with water, brine, dried and evaporated under reduced pressure. The residue was dissolved in DCM (10 ml) then trifluoroacetic acid (10 ml) added and stirred for 18 h at RT. The reaction mixture was evaporated to dryness and the residue purified by reverse phase HPLC followed by trituration with methanol to give a white solid. Yield 0.035 g

Workup

  1. washwashed with water, brine
  2. customdried
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in DCM (10 ml)
  5. additiontrifluoroacetic acid (10 ml) added
  6. customThe reaction mixture was evaporated to dryness
  7. customthe residue purified by reverse phase HPLC
  8. customto give a white solid

Sources & evidence

ORD record
ord-d9685bb7172045d1a3213f0cd911f255
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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