Hydrochloric Acid → HCID 66671696, compound

HRID 446570Notes

Reaction equation

HRID 446570 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:31])[CH2:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](OCC)=[O:27])=[CH:16][CH:15]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.[C:35]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42](=[O:54])[O:43][CH:44]1[CH2:49][CH2:48][N:47]([CH2:50][CH2:51][NH:52][CH3:53])[CH2:46][CH2:45]1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(O)C.O.ClCCl>[C:35]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42](=[O:54])[O:43][CH:44]1[CH2:49][CH2:48][N:47]([CH2:50][CH2:51][N:52]([C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:17]2[CH:18]=[CH:19][C:14]([C:12](=[O:13])[CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:31])=[CH:15][CH:16]=2)[CH3:53])[CH2:46][CH2:45]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamateHCID 66793634HCID 66793634, compound

Product 1

HCID 66671696HCID 66671696, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (470 mg, 1.08 mmol) obtained in Example 77b was dissolved in a mixed solvent of ethanol (5 mL) and water (5 mL), a 1 N aqueous sodium hydroxide solution (1.62 mL, 1.62 mmol) was added, and the mixture was stirred at room temperature. After the reaction was completed, a 1 N aqueous hydrochloric acid solution was added, and then the mixture was extracted with dichloromethane (×3). The solvent was evaporated under reduced pressure, the resulting residue and 1-[2-(methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (346 mg, 0.981 mmol) were dissolved in dichloromethane (10 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (375 mg, 1.96 mmol) was added, and the mixture was stirred at room temperature for 14 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with dichloromethane (×3). The resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, then the residue was purified by NH silica gel column chromatography (elution solvents, hexane:ethyl acetate=9:1→1:1→0:1, v/v) and then by silica gel column chromatography (elution solvents, ethyl acetate:methanol=10:0→9:1, v/v) to give the title compound (298 mg; yield, 41%) as a white solid.

Workup

  1. extractionthe mixture was extracted with dichloromethane (×3)
  2. customThe solvent was evaporated under reduced pressure
  3. stirringthe mixture was stirred at room temperature for 14 hours
  4. extractionthe mixture was extracted with dichloromethane (×3)
  5. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (elution solvents, hexane:ethyl acetate=9:1→1:1→0:1, v/v)
  8. washby silica gel column chromatography (elution solvents, ethyl acetate:methanol=10:0→9:1, v/v)

Sources & evidence

ORD record
ord-17210f02eaab431ca195e16bbf41f2b4
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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