1-Hydroxybenzotriazole → HCID 57507775, compound

HRID 605813Notes

Reaction equation

HRID 605813 reaction equation
Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:23][C:24]([C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32]([OH:34])=O)=[CH:28][CH:27]=1)=[O:25].Cl.Cl.[N:39]1([C:45]([O:47][C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:23][C:24]([C:26]1[CH:27]=[CH:28][C:29]([O:30][CH2:31][C:32]([CH:42]2[CH2:43][CH2:44][N:39]([C:45]([O:47][C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)=[O:46])[CH2:40][CH2:41]2)=[O:34])=[CH:35][CH:36]=1)=[O:25]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 35453662-(4-carbamoylphenoxy)acetic AcidHCID 67067047HCID 67067047, compound

Product 1

HCID 57507775HCID 57507775, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TEA (0.251 ml), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (259 mg), 1-hydroxybenzotriazole (122 mg) and the above-produced compound [4-(aminocarbonyl)phenoxy]acetic acid (184 mg) were added to a DMF (5 ml) solution containing 3-pyridyl 1-piperidinecarboxylate dihydrochloride (252 mg) obtained in the method of Example 121, followed by stirring at room temperature for 5 hours. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=95:5 (v/v)), and the resulting solid was recrystallized from EtOAc/acetonitrile to obtain pyridin-3-yl 4-{[4-(aminocarbonyl)phenoxy]acetyl}piperidine-1-carboxylate (274 mg).

Workup

  1. customobtained in the method of Example 121
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=95:5 (v/v))
  6. customthe resulting solid was recrystallized from EtOAc/acetonitrile

Sources & evidence

ORD record
ord-22ad62655870447aa5ea4d8b55df78ba
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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