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 2268377ノート

反応式

HRID 2268377 の反応式
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

参加物

4

反応物 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

生成物 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-furandiol収率 25.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

{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+).

後処理

  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)

出典と根拠

ORDレコード
ord-06e1dd9952a44b2f93121ec4bb9e571c
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

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