Ethylamine hydrochloride → HCID 67056576, compound

HRID 546537Notes

Reaction equation

HRID 546537 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.[CH2:37]([NH2:39])[CH3:38].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(N(CC)CC)C>[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])[NH:39][CH2:37][CH3:38])[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 4

HCID 11198Ethylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 44593556HCID 44593556, compound

Product 1

HCID 67056576HCID 67056576, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

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 (150 mg) was dissolved in N,N-dimethylformamide (3 ml), to which N-ethylamine hydrochloride (119 mg), 1-hydroxybenzotriazole monohydrate (79 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (112 mg) and triethylamine (326 μl) were added, and the mixture was stirred at room temperature for 4 days. 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 (171 μl) 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 (74 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 (171 μl) 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-b97107866f184755a5777e5f14c4d932
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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