Diisopropylethylamine → HCID 86726719, compound

HRID 1499489Notes

Reaction equation

HRID 1499489 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.[CH3:14][C@H:15]1[CH2:20][NH:19][CH2:18][C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16]1.CCN(C(C)C)C(C)C>CCO>[CH3:14][C@H:15]1[CH2:20][N:19]([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)[CH2:18][C@@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57433105tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamateHCID 867266754-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine

Product 1

HCID 86726719HCID 86726719, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave vial containing 4-iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine (from Example 9, step 3) (47.8 mg, 0.164 mmol) and tert-butyl [(3S,5R)-5-methylpiperidin-3-yl]carbamate (33.7 mg, 0.157 mmol), EtOH (1.00 mL) was added, followed by DIPEA (41.5 mg, 0.321 mmol). The mixture was heated under microwave irradiation at 100° C. for 2 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the title compound as a yellow solid (44.5 mg, 75%). LCMS calc. for C18H27N4O5 (M+H)+: m/z=379.2. found 379.2.

Workup

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

Sources & evidence

ORD record
ord-abc8d633c63e49b6a8e4d2e94cb5f488
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

Loading…