2-Morpholinoethylamine → HCID 86588183, compound

HRID 2297678Notes

Reaction equation

HRID 2297678 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[CH:18]=[C:17]([CH2:19][CH3:20])[O:16][N:15]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([Cl:36])=[N:25][C:26]=2[NH:30][CH:31]([CH2:34][CH3:35])[CH2:32][CH3:33])(=[O:3])C.O1CCN(CCN)CC1>CS(C)=O>[CH:1]([OH:4])=[O:3].[Cl:36][C:24]1[N:23]=[C:22]2[C:27]([N:28]=[CH:29][N:21]2[C@H:6]2[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]3[CH:18]=[C:17]([CH2:19][CH3:20])[O:16][N:15]=3)[O:7]2)=[C:26]([NH:30][CH:31]([CH2:32][CH3:33])[CH2:34][CH3:35])[N:25]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 86588182HCID 86588182, compound

Product 1

HCID 86588183HCID 86588183, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of (2R,3R,4R,5R)-4-(acetyloxy)-2-{2-chloro-6-[(1-ethylpropyl)amino]-9H-purin-9-yl}-5-(5-ethylisoxazol-3-yl)tetrahydrofuran-3-yl acetate (30 mg) and 2-morpholinoethylamine (0.037 ml) was heated at 90° C. for 24 h in dimethylsulphoxide (0.5 ml). Heating was continued for 60 h at 90° C. Purification by preparative HPLC (gradient profile 5-95% (ii) over 18.25 min) gave the title compound as a white solid (6 mg).

Workup

  1. temperatureHeating
  2. customPurification by preparative HPLC (gradient profile 5-95% (ii) over 18.25 min)

Sources & evidence

ORD record
ord-284b46e7d5b349b3819be9f1d8c26a70
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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