Diisopropylethylamine → HCID 21106456, compound

HRID 1765058Notes

Reaction equation

HRID 1765058 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH:12]=[N:11][C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:9]2)[CH:3]=1.[NH2:20][C@H:21]1[CH2:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]1.CCN(C(C)C)C(C)C>O1CCOCC1.C(OCC)(=O)C>[C:14]1([NH:13][C:10]2[N:11]=[CH:12][N:8]([C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:20][CH:21]4[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]4)[CH:3]=3)[N:9]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 21106441HCID 21106441, compound

Product 1

HCID 21106456HCID 21106456, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of [1-(6-Chloro-pyrimidin-4-yl)-1H-[1,2,4]triazol-3-yl]-phenyl-amine (0.25 mmol) in dioxane (5 ml), was added some (S)-3-amino-N-boc-piperidine (1 mmol, 4 equivalents) and DIPEA (1 mmol, 4 equivalents). The reaction mixture was stirred at 80° C. for two hours then 100° C. for eighteen hours. The reaction mixture was diluted with ethyl acetate (50 ml). The organic layer was washed with 10% citric acid, saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate. Filtrated and the organic layer was concentrated in vacuo to afford a pale yellow solid.

Workup

  1. wait100° C. for eighteen hours
  2. washThe organic layer was washed with 10% citric acid, saturated sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationFiltrated
  5. concentrationthe organic layer was concentrated in vacuo
  6. customto afford a pale yellow solid

Sources & evidence

ORD record
ord-1b959ffa9fc84f8bb0a2dd56ddd5d8b5
Source dataset
uspto-grants-2007_06
Patent number
US07226920B2

Reaction notes

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