Cesium carbonate → HCID 118308324, compound

HRID 1750576Notes

Reaction equation

HRID 1750576 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[N:17]1[N:21]=[CH:20][CH:19]=[N:18]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:76]1[N:81]=[CH:80][C:79]([CH2:82][CH3:83])=[CH:78][N:77]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH2:82]([C:79]1[CH:78]=[N:77][C:76]([NH:2][C@H:3]2[CH2:7][CH2:6][CH2:5][C@@H:4]2[NH:8][C:9](=[O:22])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[N:17]2[N:18]=[CH:19][CH:20]=[N:21]2)=[N:81][CH:80]=1)[CH3:83]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 35727632-Chloro-5-ethylpyrimidineHCID 118308085HCID 118308085, compound2×

Product 1

HCID 118308324HCID 118308324, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-[(1S,2S)-2-aminocyclopentyl]-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 7; 100 mg, 0.31 mmol), toluene (1 ml), BINAP (19 mg, 0.03 mmol), cesium carbonate (404 mg, 0.12 mmol) and 2-chloro-5-ethylpyrimidine (CAS number 111196-81-7; 48 mg, 0.34 mmol) was purged with nitrogen gas for 5 minutes before tris(dibenzylideneacetone)dipalladium(0) (14 mg, 0.02 mmol) was added. The reaction mixture was stirred at 100° C. for 15 hours and upon cooling poured into water (3 ml) and extracted with ethyl acetate (3×10 ml). The combined organics were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Workup

  1. additionwas added
  2. temperatureupon cooling
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia)

Sources & evidence

ORD record
ord-de59ac0ecc0946c0a686139b19af9dc3
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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