Triethylamine → HCID 58840840, compound

HRID 1268713Notes

Reaction equation

HRID 1268713 reaction equation
[CH3:1][NH:2][C:3]([C@@:5]1(N2C=NC3C2=NC(Cl)=NC=3Cl)[C@@H:12]2[C@@H:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[CH2:7][S:6]1)=[O:4].Cl.IC1C=C(C=CC=1)CN.C(N(CC)CC)C>C(O)C>[CH3:1][NH:2][C:3]([CH:5]1[CH:12]2[CH:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[CH2:7][S:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27238613-Iodobenzylamine hydrochlorideHCID 87826652HCID 87826652, compound

Product 1

HCID 58840840HCID 58840840, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

65 mg (0.16 mmol) of (3aS,4R,6aR)-4-(2,6-dichloropurin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4-carboxylic acid methyl amide from the aforementioned Experimental Example 10, 55 mg (0.20 mmol) of 3-iodobenzylamine hydrochloride, and 0.065 mL (0.46 mmol) of triethylamine were added to ethanol and stirred at ambient temperature for 3 days. The reaction mixture was distilled under reduced pressure to obtain a concentrate. The concentrate was purified by silica gel column chromatography using the eluant (hexane:ethyl acetate=1:1) to obtain 87 mg (yield: 90%) of (3aS,4R,6aR)-4-[2-chloro-6-(3-iodobenzylamino)purin-9-yl)]-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4-carboxylic acid methyl amide as a white foam.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto obtain a concentrate
  3. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3ad4fbfdca9642ea924e2e23d8ada7d4
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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