1H-1,2,4-Triazole → HCID 59178869, compound

HRID 2093458Notes

Reaction equation

HRID 2093458 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([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:3]=1.[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.C(OCC)(=O)C>[N:27]1([C:2]2[N:7]=[CH:6][N:5]=[C:4]([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:3]=2)[CH:31]=[N:30][CH:29]=[N:28]1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 59178818HCID 59178818, compound

Product 1

HCID 59178869HCID 59178869, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

The tert-butyl 1′-(6-chloropyrimidin-4-yl)-4,4′-bipiperidine-1-carboxylate (190 mg, 0.50 mmol), 1,2,4-triazole (69 mg, 1.0 mmol), cesium carbonate (488 mg, 1.5 mmol) were added in NMP (5 mL) and heated to 140° C. for 1.5 hours. The reaction crude were cooled down to r.t. and diluted with ethyl acetate (10 mL), washed with water (5 mL, ×1) and brine (5 mL, ×1). The organic phase was dried over magnesium sulfate, filtered and concentrated on rotavapor. The crude mixture was purified by preparative TLC with 50% ethyl acetate:hexane to yield the title compound.

Workup

  1. customThe reaction crude
  2. temperaturewere cooled down to r.t.
  3. washwashed with water (5 mL, ×1) and brine (5 mL, ×1)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on rotavapor
  7. customThe crude mixture was purified by preparative TLC with 50% ethyl acetate

Sources & evidence

ORD record
ord-33b91ddb203944309f8199f7735cb430
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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