N-(2-Aminoethyl)piperidine → (2R,3R,4S,5R)-2-[6-[(2,2-Diphenylethyl)amino]-2-({[2-(1-piperidinyl)ethyl]amino}methyl)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268377Notes

Reaction equation

HRID 2268377 reaction equation
CS(O[CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)=[C:9]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]=1)(=O)=O.[N:41]1([CH2:47][CH2:48][NH2:49])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>ClCCl>[C:29]1([CH:28]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:27][NH:26][C:9]2[N:8]=[C:7]([CH2:6][NH:49][CH2:48][CH2:47][N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

Product 1

HCID 9808835(2R,3R,4S,5R)-2-[6-[(2,2-Diphenylethyl)amino]-2-({[2-(1-piperidinyl)ethyl]amino}methyl)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (150 mg, 0.26 mmol) (Preparation 25) was dissolved in stirred dichloromethane (5 ml) and 2-(1-piperidinyl)ethylamine (0.2 ml, 1.3 mmol) added. The reaction mixture was stirred for 24 hr at room temperature. The solvent was removed from the reaction mixture under reduced pressure and the residue partitioned between dichloromethane (100 ml) and water (50 ml). The organic layer was separated and washed with water (50 ml), followed by removal of solvent under reduced pressure and purification of the residue by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (95:5) increasing in polarity to dichloromethane:methanol:ammonia (90:10:1). This gave title compound (40 mg) as a gum. MS: 603 (MH+).

Workup

  1. customThe solvent was removed from the reaction mixture under reduced pressure
  2. customthe residue partitioned between dichloromethane (100 ml) and water (50 ml)
  3. customThe organic layer was separated
  4. washwashed with water (50 ml)
  5. customfollowed by removal of solvent under reduced pressure and purification of the residue by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (95:5)
  6. temperatureincreasing in polarity to dichloromethane:methanol:ammonia (90:10:1)

Sources & evidence

ORD record
ord-06e1dd9952a44b2f93121ec4bb9e571c
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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