Diisopropylethylamine → HCID 86726737, compound

HRID 1499506Notes

Reaction equation

HRID 1499506 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.[F:14][C:15]([F:31])([F:30])[C@H:16]1[CH2:21][NH:20][CH2:19][C@@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]1.CCN(C(C)C)C(C)C>CCO>[N+:8]([C:7]1[C:2]([N:20]2[CH2:21][C@H:16]([C:15]([F:31])([F:30])[F:14])[CH2:17][C@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:19]2)=[C:3]2[CH2:13][CH2:12][O:11][C:4]2=[N:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 73977851tert-butyl N-[(3S,5R)-5-(trifluoromethyl)piperidin-3-yl]carbamateHCID 867266754-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine

Product 1

HCID 86726737HCID 86726737, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 4-iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine (238.2 mg, 0.8157 mmol) and tert-butyl [(3S,5R)-5-(trifluoromethyl)piperidin-3-yl]carbamate (from MolBridge, 203.9 mg, 0.7600 mmol) was added EtOH (3.0 mL), followed by DIPEA (539.5 mg, 4.174 mmol). The mixture was stirred at 120° C. for 18 h. After cooling to room temperature, the reaction was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-50% EtOAc in hexanes) to afford the sub-title compound as a yellow solid (227.1 mg, 69%). LCMS calc. for C18H24F3N4O5 (M+H)+: m/z=433.2. found 433.2.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d3e1dd51ac354c5e88747e21686bdf43
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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