Cesium carbonate → HCID 59276262, compound

HRID 2070887Notes

Reaction equation

HRID 2070887 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:32]=[C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([NH:18][C@H:19]4[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]4)[N:12]3[N:11]=2)=[CH:5][CH:4]=1)#[N:2].BrC1N2N=C(NC3C=CC(C#N)=CC=3)N=C2C=CC=1.N[C@H]1CCCN(C(OC(C)(C)C)=[O:60])C1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.[Cl-].[Na+].O>[NH:21]1[CH2:22][CH2:23][CH2:24][C@H:19]([NH:18][C:17]2[N:12]3[N:11]=[C:10]([NH:9][C:6]4[CH:7]=[CH:8][C:3]([C:1]([NH2:2])=[O:60])=[CH:4][CH:5]=4)[N:32]=[C:13]3[CH:14]=[CH:15][CH:16]=2)[CH2:20]1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 70921797HCID 70921797, compoundHCID 86640816HCID 86640816, compound

Product 1

HCID 59276262HCID 59276262, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

(S)-tert-Butyl 3-(2-(4-cyanophenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)piperidine-1-carboxylate. To an orange solution of 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzonitrile (0.250 g, 0.796 mmol) in dioxane (10 mL) was added (5)-tert-butyl 3-aminopiperidine-1-carboxylate (0.319 g, 1.592 mmol), cesium carbonate (0.519 g, 1.592 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.092 g, 0.159 mmol) and tris(dibezylideneacetone)palladium (0.077 g, 0.084 mmol) at room temperature under nitrogen. The reaction mixture was heated at 100° C. for 1.5 h under nitrogen. Upon completion of the reaction as indicated by LCMS the reaction mixture was poured into brine, and extracted with ethyl acetate several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by column chromatography (eluting with 0-80% ethyl acetate in hexanes) to give the title compound as a tan solid (0.122 g, 35% yield). MS (ESI) m/z 434.51 [M+1]+.

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with ethyl acetate several times
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude mixture was purified by column chromatography (eluting with 0-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-35141bedf6b6487eb615d7840f9bc698
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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