Cesium carbonate → HCID 9930204, compound

HRID 413431Notes

Reaction equation

HRID 413431 reaction equation
[NH2:1][C:2]([C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24](F)[CH:23]=1)([C:16]1[N:17]([CH3:21])[CH:18]=[N:19][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:1][C:2]1([C:16]2[N:17]([CH3:21])[CH:18]=[N:19][CH:20]=2)[C:22]2=[CH:29][C:28](=[C:25]([C:26]#[N:27])[CH:24]=[CH:23]2)[O:15][C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[CH2:8][O:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 18533202HCID 18533202, compound

Product 1

HCID 9930204HCID 9930204, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[1-Amino-5-(3-hydroxy-benzyloxy)-1-(3-methyl-3H-imidazol-4-yl)-pentyl]-2-fluoro-benzonitrile (0.214 g, 0.443 mmol) was dissolved in DMF (44 mL) at ambient temperature and treated with Cs2CO3 (0.577 g, 1.77 mmol). After 18 h, the reaction mixture was concentrated to dryness, and partitioned between a minimum amount of H2O and CH2Cl2. The aqueous layer was washed with CH2Cl2 (2×), the organics combined, dried (MgSO4), filtered and concentrated to give the title compound after purification on the ISCO Combiflash eluting with 1-3% MeOH/CH2Cl2w/NH4OH. MS (M+1) 389.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. custompartitioned between a minimum amount of H2O and CH2Cl2
  3. washThe aqueous layer was washed with CH2Cl2 (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55b00ccf8b8f48888b8c6c2d70cf2735
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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