Hydrochloric Acid → HCID 86761916, compound

HRID 446582Notes

Reaction equation

HRID 446582 reaction equation
[NH2:1][C:2]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=O)=[S:3].[OH-].[Na+].Cl.[C:17]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:36])[O:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][CH3:35])[CH2:28][CH2:27]1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CO>[C:17]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:36])[O:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][N:34]([C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:2]([NH2:1])=[S:3])[CH3:35])[CH2:28][CH2:27]1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4962408methyl 6-[(aminocarbonothioyl)amino]hexanoateHCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

Product 1

HCID 86761916HCID 86761916, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 6-[(aminocarbonothioyl)amino]hexanoate (335 mg, 1.64 mmol) was dissolved in methanol (10 mL), a 1 N aqueous sodium hydroxide solution (2.46 mL, 2.46 mmol) was added, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, 1 N hydrochloric acid (2.46 mL, 2.46 mmol) was added, and then the solvent was evaporated under reduced pressure. The resulting residue was dissolved in dichloromethane, 1-[2-(methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (578 mg, 1.64 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (469 mg, 2.46 mmol) and triethylamine (0.342 mL, 2.46 mmol) were added, and the mixture was stirred overnight at room temperature. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, the mixture was extracted 3 times with methylene chloride, and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (elution solvents, n-hexane:ethyl acetate:methanol=1:1:0→0:10:0→0:9:1, v/v/v) to give the title compound (291 mg; yield, 34%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in dichloromethane
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionthe mixture was extracted 3 times with methylene chloride
  5. dry with materialthe resulting organic layer was dried with anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by NH silica gel column chromatography (elution solvents, n-hexane:ethyl acetate:methanol=1:1:0→0:10:0→0:9:1, v/v/v)

Sources & evidence

ORD record
ord-9bd726d10d004918996dad66a65b89d3
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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