Benzenesulfonyl chloride → HCID 10231807, compound

HRID 1700087Notes

Reaction equation

HRID 1700087 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13]2)=[C:5]([NH:21][CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[N:4]=1.C(N(CC)CC)C.[C:40]1([S:46](Cl)(=[O:48])=[O:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCOCC1>[NH3:1].[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13][C@H:12]1[N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([CH2:2][NH:1][S:46]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:48])=[O:47])=[N:4][C:5]=2[NH:21][CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 59875475HCID 59875475, compound

Product 2

HCID 222AmmoniaHCID 10231807HCID 10231807, compoundYield 140.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(1-naphthylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol (0.16 g, 0.37 mmol) (Preparation 15) in dioxan (28 ml) was heated gently until a solution was achieved. The solution was cooled to room temperature and treated with triethylamine (0.12 g, 1.19 mmol) followed by addition of a solution of benzenesulphonyl chloride (0.060 g, 0.34 mmol) in dioxan (2 ml) over 10 minutes. The mixture was then stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure and the residue azeotroped with dichloromethane. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (92:8:0.4 by volume) to afford the title compound as a white solid (150 mg).

Workup

  1. temperaturewas heated gently until a solution
  2. customThe solvent was removed under reduced pressure
  3. customthe residue azeotroped with dichloromethane
  4. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-6e9f7b6143854ddfa5e93c77757dbf70
Source dataset
uspto-grants-2002_02
Patent number
US06350735B1

Reaction notes

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