Triethylamine → HCID 59975281, compound

HRID 2268359Notes

Reaction equation

HRID 2268359 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][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.[CH3:37][O:38][CH2:39][CH2:40][S:41](Cl)(=[O:43])=[O:42].C(N(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][NH:1][S:41]([CH2:40][CH2:39][O:38][CH3:37])(=[O:43])=[O:42])=[N:4][C:5]=2[NH:22][CH2:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=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 134802212-Methoxyethane-1-sulfonyl chloride

Product 1

HCID 59975281HCID 59975281, compoundYield 74.9%

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) (250 mg, 0.49 mmol), 2-methoxy-1-ethanesulfonyl chloride (J. Org. Chem. 2633, 26, 1961) (77 mg, 0.49 mmol), triethylamine (150 mg, 1.5 mmol) in tetrahydrofuran (23 ml). The crude product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (96:4:0.2) gave the title compound (225 mg) as an oil. MS: 614 (MH+).

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (96:4:0.2)

Sources & evidence

ORD record
ord-b859b4d8eaf54fc5aaa49ae3180620ce
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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