Dimethylamine, hydrochloride → HCID 9808345, compound

HRID 2104449Notes

Reaction equation

HRID 2104449 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 away under reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The resultant organic layer was washed with saturated brine and dried over magnesium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the resultant residue was purified by silica gel column chromatography (methylene chloride:methanol=93:7). The thus-obtained colorless solids (135 mg) were suspended in ethanol (5 mL), and then 1N HCl in ethanol (0.5 mL) was added. The mixture was stirred for 2 hours, and the solvent was distilled away to give the title compound (112 mg).

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washThe resultant organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate anhydrate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe resultant residue was purified by silica gel column chromatography (methylene chloride:methanol=93:7)
  8. addition1N HCl in ethanol (0.5 mL) was added
  9. stirringThe mixture was stirred for 2 hours
  10. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-1207299171af4db98205e85bc973c1de
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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