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Benzenesulfonyl chloride → N-(2-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)benzenesulfonamide

HRID 2268388
Notes
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Reaction equation

HRID 2268388 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@H:13]2[C@H:17]([OH:18])[C@H:16]([OH:19])[C@@H:15]([CH2:20][O:21][CH3:22])[O:14]2)=[C:6]([NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:5]=1.[C:38]1([S:44](Cl)(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C>>[OH:18][C@@H:17]1[C@H:16]([OH:19])[C@@H:15]([CH2:20][O:21][CH3:22])[O:14][C@H:13]1[N:10]1[CH:9]=[N:8][C:7]2[C:11]1=[N:12][C:4]([CH2:3][CH2:2][NH:1][S:44]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:46])=[O:45])=[N:5][C:6]=2[NH:23][CH2:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 9957801(2R,3R,4S,5R)-2-{2-(2-Aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 59975303N-(2-{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)benzenesulfonamideYield 56.2%

Procedure

The title compound was prepared by a similar method to example 3 using (2R,3R,4S,5R)-2-{2-(2-aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)-tetrahydro-3,4-furandiol (example 11) (200 mg, 0.40 mmol), phenylsulfonyl chloride (70 mg, 0.40 mmol) and triethylamine (0.15 ml, 1.08 mmol). The compound was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5) to give the title compound (145 mg) as a powder. MS: 645 (MH+).

Workup

  1. customThe compound was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-3dbff345d18042dd8103dcd5486f9d15
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326359B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes