Diisopropylethylamine → HCID 86726853, compound

HRID 1499633Notes

Reaction equation

HRID 1499633 reaction equation
I[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[O:11][CH2:12][CH2:13][C:3]=12.[OH:14][C@:15]1([CH3:30])[C@@H:20]([CH3:21])[CH2:19][NH:18][CH2:17][C@H:16]1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C>CCO>[OH:14][C@:15]1([CH3:30])[C@@H:20]([CH3:21])[CH2:19][N:18]([C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]3[O:11][CH2:12][CH2:13][C:3]=23)[CH2:17][C@H:16]1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 867266754-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridineHCID 86726851HCID 86726851, compound

Product 1

HCID 86726853HCID 86726853, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a vial containing 4-iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine (59 mg, 0.20 mmol) and tert-butyl [(3R,4R,5S)-4-hydroxy-4,5-dimethylpiperidin-3-yl]carbamate (46 mg, 0.19 mmol) was added EtOH (2.0 mL), followed by DIPEA (100 mg, 0.772 mmol). The mixture was stirred at 110° C. for 15 h. After cooling to the room temperature, the reaction was concentrated under reduced pressure. The resulting residue was purified on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a yellow foamy solid (51 mg, 67%). LCMS calc. for C19H29N4O6 (M+H)+: m/z=409.2. found 409.0.

Workup

  1. temperatureAfter cooling to the room temperature
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customThe resulting residue was purified on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f7060af2bed1402ebeabd30276082e6a
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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