Ethylamine hydrochloride → HCID 57940578, compound

HRID 1437146Notes

Reaction equation

HRID 1437146 reaction equation
[CH2:1]([N:3](CC)CC)[CH3:2].[Cl:8][C:9]1[CH:10]=[C:11]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:12][N:13]1[CH2:18][CH2:17][O:16][C@@H:15]([CH2:19][NH:20][C:21](=[O:32])[NH:22][CH2:23][C:24]2[O:28][C:27]([C:29](O)=[O:30])=[CH:26][CH:25]=2)[CH2:14]1.ON1C2C=CC=CC=2N=N1.Cl.C(N)C.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH2:1]([NH:3][C:29]([C:27]1[O:28][C:24]([CH2:23][NH:22][C:21]([NH:20][CH2:19][C@@H:15]2[O:16][CH2:17][CH2:18][N:13]([CH2:12][C:11]3[CH:33]=[CH:34][C:35]([Cl:36])=[C:9]([Cl:8])[CH:10]=3)[CH2:14]2)=[O:32])=[CH:25][CH:26]=1)=[O:30])[CH3:2]

Participants

7

Reactant 5

HCID 11198Ethylamine hydrochloride2×HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 69062107HCID 69062107, compound

Product 1

HCID 57940578HCID 57940578, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 41 in N,N-dimethylformamide (2 ml) was added 1-hydroxybenzotriazole (0.0159), and ethylamine hydrochloride (0.042 g). To the suspension was added N,N-diisopropylethylamine (0.09 ml) and then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.02 g). After stirring at room temperature for 16 h, further amounts of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.030 g), ethylamine hydrochloride (0.02 g) and N,N-diisopropylethylamine (0.09 ml) were added. The mixture was stirred for a further 3 h at room temperature. The mixture was partitioned between ethyl acetate (60 ml) and 2N sodium hydroxide (20 ml) The phases were separated and the organic phase washed with 2N sodium hydroxide (20 ml) and water (20 ml), dried (MgSO4), and filtered. The solvent was removed in vacuo. The residue was dissolved in methanol and applied onto a sulphonic acid ion exchange cartridge (1 g Isolute SCX, pre-treated with methanol). The cartridge was eluted with methanol followed by 10% 0.880 ammonia in methanol. The solvent was removed from the basic fraction by evaporation under a stream of nitrogen. The residue was purified by mass directed preparative HPLC to give the title compound as a colourless gum (0.0064 g).

Workup

  1. stirringThe mixture was stirred for a further 3 h at room temperature
  2. customThe mixture was partitioned between ethyl acetate (60 ml) and 2N sodium hydroxide (20 ml) The phases
  3. customwere separated
  4. washthe organic phase washed with 2N sodium hydroxide (20 ml) and water (20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. dissolutionThe residue was dissolved in methanol
  9. additionapplied onto a sulphonic acid ion exchange cartridge (1 g Isolute SCX, pre-treated with methanol)
  10. washThe cartridge was eluted with methanol
  11. customThe solvent was removed from the basic fraction by evaporation under a stream of nitrogen
  12. customThe residue was purified by mass

Sources & evidence

ORD record
ord-a436ef284c5e469dadf83784e7537a2b
Source dataset
uspto-grants-2009_11
Patent number
US07622464B2

Reaction notes

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