Triethylamine → {9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yimethyl)(tetrahydro-2H-pyran-4-yl)methanesulfonamide

HRID 2268360Notes

Reaction equation

HRID 2268360 reaction equation
N[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][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.[O:37]1[CH2:42][CH2:41][CH:40]([CH2:43][S:44](Cl)(=[O:46])=[O:45])[CH2:39][CH2:38]1.C([N:50](CC)CC)C>O1CCCC1>[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[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][CH:43]([CH:40]1[CH2:41][CH2:42][O:37][CH2:38][CH2:39]1)[S:44]([NH2:50])(=[O:46])=[O:45])=[N:4][C:5]=2[NH:22][CH2:23][CH:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolHCID 18348392(Oxan-4-yl)methanesulfonyl chloride

Product 1

HCID 86757640{9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yimethyl)(tetrahydro-2H-pyran-4-yl)methanesulfonamideYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by a similar method to example 3 using (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (245 mg, 0.48 mmol), tetrahydro-2H-pyran-4-ylmethanesulfonyl chloride (preparation 21) (95 mg, 0.48 mmol), triethylamine (145 mg, 1.44 mmol) in tetrahydrofuran (23 ml). Purification by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.25) gave the title compound as an oil (118 mg). MS: 654 (MH+).

Workup

  1. customPurification by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.25)

Sources & evidence

ORD record
ord-00bcf32d5a954f5884a49cc89fbd1feb
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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