Dimethylamine, hydrochloride → HCID 9808345, compound

HRID 902896Notes

Reaction equation

HRID 902896 reaction equation
Cl.[CH3:2][NH:3][CH3:4].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:38]([NH:40][C@@H:41]1[CH2:46][CH2:45][C@@H:44]([C:47]([OH:49])=O)[CH2:43][C@@H:42]1[NH:50][C:51]([C:53]1[S:54][C:55]3[CH2:56][N:57]([CH3:62])[CH2:58][CH2:59][C:60]=3[N:61]=1)=[O:52])=[O:39])=[CH:32]2>C(Cl)(Cl)Cl.C(N(CC)CC)C>[ClH:28].[Cl:28][C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:38]([NH:40][C@H:41]1[CH2:46][CH2:45][C@H:44]([C:47]([N:3]([CH3:4])[CH3:2])=[O:49])[CH2:43][C@H:42]1[NH:50][C:51]([C:53]1[S:54][C:55]3[CH2:56][N:57]([CH3:62])[CH2:58][CH2:59][C:60]=3[N:61]=1)=[O:52])=[O:39])=[CH:32]2

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68446914HCID 68446914, compound

Product 1

HCID 9808345HCID 9808345, compoundYield 118.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (0.25 ml), dimethylamine hydrochloride (133 mg), 1-hydroxybenzotriazole monohydrate (53 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (75 mg) were added to a chloroform suspension (10 ml) of the compound (168 mg) obtained in Example 56, and the mixture was stirred for 72 hours. The solvent was distilled off under reduced pressure, and water was added to the residue to conduct extraction with chloroform. The resultant organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel (methylene chloride:methanol=93:7). The thus-obtained colorless solids (135 mg) were suspended in ethanol (5 ml), to which 1N ethanol solution (0.5 ml) of hydrochloric acid was added. The mixture was stirred for 2 hours, and the solvent was distilled off to obtain the title compound (112 mg).

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionextraction with chloroform
  4. washThe resultant organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resultant residue was purified by column chromatography on silica gel (methylene chloride:methanol=93:7)
  8. additionwas added
  9. stirringThe mixture was stirred for 2 hours
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-54b33c07fc07456ca5c98d0cdd7da039
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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