N-(2-Aminoethyl)piperidine → HCID 178465183, compound

HRID 897076Notes

Reaction equation

HRID 897076 reaction equation
[C:1]([N:3]=[C:4](SC)SC)#[N:2].[NH2:9][CH2:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@@H:20]2[O:24][C@H:23]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])[C@@H:22]([OH:30])[C@H:21]2[OH:31])=[C:13]([NH:32][CH2:33][CH:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:12]=1.[NH2:47][CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1>C(O)C>[NH3:2].[C:1](/[N:3]=[C:4](/[NH:9][CH2:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@@H:20]2[O:24][C@H:23]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])[C@@H:22]([OH:30])[C@H:21]2[OH:31])=[C:13]([NH:32][CH2:33][CH:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:12]=1)\[NH:47][CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1)#[N:2]

Participants

6

Reactant 3

HCID 33944N-(2-Aminoethyl)piperidine2×HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 59909598(2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

Product 2

HCID 222AmmoniaHCID 178465183HCID 178465183, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dimethyl cyanodithioimidocarbonate (77 mg, 0.48 mmol) was added to a solution of (2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (250 mg, 0.48 mmol) (Preparation 11) in ethanol 10 ml). The reaction mixture was stirred for 3 hours at room temperature and then 2-aminoethylpiperidine (88 μl, 0.68 mmol) was added. The reaction mixture was heated under reflux for 2 hours, more 2-aminoethylpiperidine (0.17 ml, 1.2 mmol) was added and then the reaction mixture was heated under reflux for a further 4 hours. The reaction was cooled and evaporated to dryness and the residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume) to give the title compound (64 mg) a foam.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for a further 4 hours
  5. temperatureThe reaction was cooled
  6. customevaporated to dryness
  7. customthe residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 by volume)
  8. temperatureincreasing in polarity to dichloromethane

Sources & evidence

ORD record
ord-5cd7dfd82e5c4e82a25a976fcf1df875
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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