HCID 68828337, compound → HCID 11570771, compound

HRID 2099352Notes

Reaction equation

HRID 2099352 reaction equation
[Cl:1][C:2]1[CH:47]=[CH:46][C:5]([CH2:6][C@@H:7]([NH:32][CH:33]2[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]2)[C:8]([N:10]2[CH:15]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH:13]([N:18]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])[CH2:14]3)=[O:9])=[CH:4][CH:3]=1>Cl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:47]=[CH:46][C:5]([CH2:6][C@H:7]([C:8]([N:10]2[CH:15]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH:13]([N:18]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:19]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[O:20])[CH2:14]3)=[O:9])[NH:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68828337HCID 68828337, compound

Product 1

HCID 11570771HCID 11570771, compoundYield 161.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

0.37 g of tert-butyl 4-{[(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]amino}-8-azabicyclo[3.2.1]oct-8-yl)-2-oxoethyl]amino}-piperidine-1-carboxylate is solubilized in 2.74 ml of 2N hydrochloric acid in diethyl ether. The reaction medium is stirred at ambient temperature for 16 h. After evaporation to dryness, the crude is chromatographed on silica gel, elution being carried out with a 95/5/0.5 mixture of dichloromethane, methanol and aqueous ammonia. 0.27 g of N-[8-(4-chloro-N-piperidin-4-yl-D-phenylalanyl)-8-azabicyclo-[3.2.1]oct-3-yl]-N-cyclohexyl-N′,N′-diethylurea hydrochloride is then obtained.

Workup

  1. customAfter evaporation to dryness
  2. customthe crude is chromatographed on silica gel, elution
  3. additionbeing carried out with a 95/5/0.5 mixture of dichloromethane, methanol and aqueous ammonia

Sources & evidence

ORD record
ord-8ea7520a4b1e4b03afd66ce1733249df
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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