Triethylamine → HCID 66793822, compound

HRID 446618Notes

Reaction equation

HRID 446618 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](OC)=[O:17])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:37](=[O:49])[O:38][CH:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][NH:47][CH3:48])[CH2:41][CH2:40]1.[CH2:56](N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:30]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][C:37]([O:38][CH:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][N:47]([CH3:48])[C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][N:8]([CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([O:27][CH3:56])=[O:26])=[CH:23][CH:22]=3)[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:11][CH:12]=2)=[O:17])[CH2:41][CH2:40]1)=[O:49]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamateHCID 66671536HCID 66671536, compound

Product 1

HCID 66793822HCID 66793822, compoundYield 98.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (233 mg, 0.58 mmol) obtained in Example 100c was dissolved in 6.0 mL of dichloromethane, and 1-[2-(methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (227 mg, 0.64 mmol) and triethylamine (163 μL, 1.17 mmol) were added. The mixture was ice cooled, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (168 mg, 0.88 mmol) and 4-(dimethylamino)pyridine (10 mg, 0.082 mmol) were added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture to dilute the mixture, and the organic layer was washed with water and a saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried with anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure, and the resulting yellow oily substance was purified by NH silica gel chromatography (n-hexane:ethyl acetate, 50:50→20:80, v/v) to give the title compound (420 mg; yield, 98%) as a white solid.

Workup

  1. temperaturecooled
  2. additionto dilute the mixture
  3. washthe organic layer was washed with water
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe resulting yellow oily substance was purified by NH silica gel chromatography (n-hexane

Sources & evidence

ORD record
ord-f35da47e78fb4bffad6665eaea9c5b3b
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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