Cesium carbonate → HCID 68580921, compound

HRID 2235005Notes

Reaction equation

HRID 2235005 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]([OH:18])=[O:17])[CH2:10][CH2:9]1.Cl[C:28]1[N:33]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:31]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:30][N:29]=1>CN(C)C=O>[C:23]([O:22][C:20]([NH:19][C@@H:15]([CH2:14][CH:11]1[CH2:10][CH2:9][CH:8]([NH:7][C:28]2[N:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:31]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:30][N:29]=2)[CH2:13][CH2:12]1)[C:16]([OH:18])=[O:17])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 126742762-Chloro-4,5-diphenylpyrimidineHCID 18639748HCID 18639748, compound

Product 1

HCID 68580921HCID 68580921, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

550 mg (1.69 mmol) of cesium carbonate were added to a solution of 161 mg (0.56 mmol) of (S)-3-(4-aminocyclohexyl)-2-tert-butoxycarbonylaminopropionic acid in 3 ml of dimethylformamide, and the mixture was stirred at room temperature. After 30 minutes, a solution of 100 mg (0.38 mmol) of 2-chloro-4,5-diphenylpyrimidine in 2 ml of dimethylformamide was added, and the mixture was stirred at 90° C. for 6 hours. The solvent was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated under high vacuum. The residue was separated by a preparative HPLC (Purosphere, gradient acetonitrile/(water+0.5% TFA), gradient 20% acetonitrile to 100% in 30 minutes). 22 mg of (S)-2-tert-butoxycarbonylamino-3-[4-(4,5-diphenylpyrimidin-2-ylamino)cyclohexyl]propionic acid were obtained. The product obtained in this way was stirred with 50% trifluoroacetic acid in acetonitrile for 16 hours, mixed with water and freeze dried. 17 mg (11%) of the desired product were obtained.

Workup

  1. stirringthe mixture was stirred at 90° C. for 6 hours
  2. concentrationThe solvent was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic phase was dried
  5. concentrationconcentrated under high vacuum
  6. customThe residue was separated by a preparative HPLC (Purosphere, gradient acetonitrile/(water+0.5% TFA), gradient 20% acetonitrile to 100% in 30 minutes)

Sources & evidence

ORD record
ord-f388c1b279184f648eb48107daec5b51
Source dataset
uspto-grants-2010_05
Patent number
US07713988B2

Reaction notes

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