Triethylamine → HCID 70155149, compound

HRID 1279206Notes

Reaction equation

HRID 1279206 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]3[O:17]C(C)(C)[O:19][C@@H:15]3[C@@H:14]([C:22]([NH:24]CC)=[O:23])[O:13]2)=[C:5]([NH:27][CH2:28][CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:4]=1.C(N([CH2:47][CH3:48])CC)C.[CH2:49]([S:52](Cl)(=[O:54])=[O:53])[CH2:50][CH3:51]>ClCCl>[C:36]1([CH:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][NH:27][C:5]2[N:4]=[C:3]([CH2:2][NH:1][S:52]([CH2:49][CH2:50][CH3:51])(=[O:54])=[O:53])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@@H:12]2[O:13][C@:14]([CH2:47][CH3:48])([C:22]([NH2:24])=[O:23])[C@@H:15]([OH:19])[C@H:16]2[OH:17])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 69558158HCID 69558158, compound

Product 1

HCID 70155149HCID 70155149, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3aS,4S,6R,6aR)-6-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (Preparation 10) (140 mg, 0.25 mmol) and triethylamine (0.05 ml, 0.36 mmol) in anhydrous dichloromethane (1 ml) was treated with a solution of 1-propanesulphonyl chloride (40 mg, 0.28 mmol) in anhydrous dichloromethane (1 ml). The mixture was stirred at room temperature for 18 hours during which time the solvent was allowed to evaporate off freely. The residue was dissolved in ethanol (1 ml), treated with hydrochloric acid (1 M, 1 ml) and heated at 60° C. for 4 hours. The solvent was removed under reduced pressure and the residue was azeotroped with ethanol (×2). The residue was then purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (95:5 by volume) gradually changing to dichloromethane:methanol (90:10 by volume) to give a solid which was triturated with diethyl ether, diluted with pentane, filtered and dried to afford the title compound as a solid (90 mg).

Workup

  1. customto evaporate off freely
  2. dissolutionThe residue was dissolved in ethanol (1 ml)
  3. additiontreated with hydrochloric acid (1 M, 1 ml)
  4. temperatureheated at 60° C. for 4 hours
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was azeotroped with ethanol (×2)
  7. customThe residue was then purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (95:5 by volume)
  8. customto give a solid which
  9. customwas triturated with diethyl ether
  10. additiondiluted with pentane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-6c633ae381204e1faeada21d6487a210
Source dataset
uspto-grants-2002_09
Patent number
US06448236B1

Reaction notes

Loading…