Dimethylamine, hydrochloride → HCID 9808345, compound

HRID 546538Notes

Reaction equation

HRID 546538 reaction equation
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([Cl:22])=[CH:17][CH:16]=3)=[O:12])[C@H:6]([NH:23][C:24]([C:26]2[S:27][C:28]3[CH2:29][N:30]([CH3:35])[CH2:31][CH2:32][C:33]=3[N:34]=2)=[O:25])[CH2:5]1)(O)=[O:2].Cl.[CH3:37][NH:38][CH3:39].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>CN(C)C=O>[ClH:22].[Cl:22][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([C:1](=[O:2])[N:38]([CH3:39])[CH3:37])[CH2:5][C@H:6]1[NH:23][C:24]([C:26]1[S:27][C:28]3[CH2:29][N:30]([CH3:35])[CH2:31][CH2:32][C:33]=3[N:34]=1)=[O:25])=[O:12])=[CH:21]2

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 44593556HCID 44593556, compound

Product 1

HCID 9808345HCID 9808345, compoundYield 153.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1S,2R,4S)-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 (900 mg) was dissolved in N,N-dimethylformamide (50 ml), to which dimethylamine hydrochloride (304 mg), 1-hydroxybenzotriazole monohydrate (262 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (369 mg) and diisopropylethylamine (1.83 ml) were added, and the mixture was stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the residue to conduct extraction with dichloromethane. The resultant organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=47:3). The thus-obtained white solid was dissolved in dichloromethane, to which 1N ethanol solution (1.49 ml) of hydrochloric acid was added. The solvent was distilled off under reduced pressure, and methanol and diethyl ether were added to the residue to collect precipitate formed by filtration, thereby obtaining the title compound (777 mg) as white solid.

Workup

  1. additionwere added
  2. distillationThe solvent was distilled off under reduced pressure
  3. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  4. extractionextraction with dichloromethane
  5. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resultant residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=47:3)
  8. dissolutionThe thus-obtained white solid was dissolved in dichloromethane, to which 1N ethanol solution (1.49 ml) of hydrochloric acid
  9. additionwas added
  10. distillationThe solvent was distilled off under reduced pressure, and methanol and diethyl ether
  11. additionwere added to the residue
  12. customto collect precipitate
  13. customformed by filtration

Sources & evidence

ORD record
ord-08e3ae1f0c1646859ca945040f7759c2
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

Loading…