Piperidine → HCID 60164413, compound

HRID 1398716Notes

Reaction equation

HRID 1398716 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=3)[C:6]=2[CH:17]=1.N1CCCCC1.[S:24]1[CH:28]=[CH:27][N:26]=[C:25]1[C:29]([OH:33])([C:31]#[CH:32])[CH3:30]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[NH2:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([N:7]2[C:6]3[CH:17]=[C:2]([C:32]#[C:31][C:29]([C:25]4[S:24][CH:28]=[CH:27][N:26]=4)([OH:33])[CH3:30])[CH:3]=[CH:4][C:5]=3[N:9]=[CH:8]2)[N:15]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 582215512-(Thiazol-2-yl)but-3-yn-2-olHCID 68181828HCID 68181828, compound

Product 1

HCID 60164413HCID 60164413, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
75 °C

Procedure

To a pressure tube was added 2-(6-bromo-1,3-benzodiazol-1-yl)pyrimidin-4-amine (300 mg, 1.03 mmol), piperidine (2 mL), tetrakis(triphenylphosphine)palladium (119.5 mg, 0.10 mmol), copper(I) iodide (19.7 mg, 0.10 mmol) and 2-(1,3-thiazol-2-yl)but-3-yn-2-ol (316.84 mg, 2.07 mmol). The reaction was stirred at 75° C. for 18 h. The reaction mixture was cooled before concentrating in vacuo. The crude product was purified by column chromatography (Biotage) eluted with DCM: methanol gradient (97:3 to 90:1). Material obtained was triturated with methanol to afford the title compound as a beige solid. (43 mg, 11.5% yield); 1H NMR (250 MHz, DMSO) delta 1.91 (3H, s), 6.41 (1H, d, J=5.79 Hz), 7.06 (1H, s), 7.37 (1H, d, J=1.52 Hz), 7.45 (2H, br. s.), 7.65-7.84 (3H, m), 8.19 (1H, d, J=5.79 Hz), 8.62 (1H, d, J=1.07 Hz), 9.00 (1H, s); LC-MS m/z+3.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationbefore concentrating in vacuo
  3. customThe crude product was purified by column chromatography (Biotage)
  4. washeluted with DCM
  5. customMaterial obtained
  6. customwas triturated with methanol

Sources & evidence

ORD record
ord-58ce15605e1c4e7092146cf0b02181e9
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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