1H-1,2,4-Triazole → HCID 24958504, compound

HRID 1947654Notes

Reaction equation

HRID 1947654 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1.CN(C)CCN.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.CN(C=O)C>[N:27]1([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][CH:11]([CH:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:31]=[N:30][CH:29]=[N:28]1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 62657Potassium Phosphate, TribasicHCID 66053N,N-DimethylethylenediamineHCID 24960700HCID 24960700, compound

Product 1

HCID 24958504HCID 24958504, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 1′-(4-iodophenyl)-4,4′-bipiperidine-1-carboxylate (17 mg, 0.036 mmol) from Step 1, 1H-1,2,4-triazole (7.5 mg, 0.108 mmol), CuI (0.7 mg, 0.0036 mmol), N,N-dimethylethane-1,2-diamine (1 mg, 0.0072 mmol), K3PO4 (16 mg, 0.0756 mmol) were mixed in a 1 dram vial, followed by addition of DMF (0.1 mL). The reaction vessel was degassed and back-filled with Ar 3 times, before it was heated at 100° C. for 20 hours. The reaction was cooled, diluted with water, extracted with EtOAc, concentrated and purified by PTLC to give the title compound.

Workup

  1. customThe reaction vessel was degassed
  2. additionback-filled with Ar 3 times, before it
  3. temperatureThe reaction was cooled
  4. additiondiluted with water
  5. extractionextracted with EtOAc
  6. concentrationconcentrated
  7. custompurified by PTLC

Sources & evidence

ORD record
ord-fdb3ef54d5e24a89ad0ace2b4113b8b4
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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