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 2268377노트

반응식

HRID 2268377 반응식
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

참가 물질

4

반응물 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

생성물 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-furandiol수율 25.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

{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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-06e1dd9952a44b2f93121ec4bb9e571c
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326359B1

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