Dimethylamine, hydrochloride → HCID 68907551, compound

HRID 546536Notes

Reaction equation

HRID 546536 reaction equation
Cl.[CH3:2][NH:3][CH3:4].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:28]([C@@H:31]1[CH2:36][CH2:35][C@@H:34]([NH:37][C:38]([C:40]2[NH:41][C:42]3[C:47]([CH:48]=2)=[CH:46][C:45]([Cl:49])=[CH:44][CH:43]=3)=[O:39])[C@@H:33]([NH:50][C:51]([C:53]2[S:54][C:55]3[CH2:56][N:57]([CH3:62])[CH2:58][CH2:59][C:60]=3[N:61]=2)=[O:52])[CH2:32]1)(O)=[O:29]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[ClH:49].[Cl:49][C:45]1[CH:46]=[C:47]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40]([C:38]([NH:37][C@@H:34]1[CH2:35][CH2:36][C@@H:31]([C:28](=[O:29])[N:3]([CH3:4])[CH3:2])[CH2:32][C@@H:33]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:48]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 68907551HCID 68907551, 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 (1R*,2S*,4R*)-4-carboxy-N1-[(5-chloroindol-2-yl)carbonyl]-N2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine (168 mg), 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 (dichloromethane:methanol=93:7). The thus-obtained colorless solid (135 mg) was suspended in ethanol (5 ml), to which 1N hydrochloric acid (0.5 ml) was added. The mixture was stirred for 2 hours, and the solvent was distilled off to obtain the title compound (112 mg) as colorless powder.

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 (dichloromethane: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-d8bbcf7150394693818f671669147e19
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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