Cesium carbonate → HCID 18629434, compound

HRID 1060899Notes

Reaction equation

HRID 1060899 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([NH:30][CH2:31][CH2:32][CH2:33][NH:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=2)(=[O:37])=[O:36])([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:17]2[N:18]([CH3:22])[CH:19]=[N:20][CH:21]=2)=[CH:12][C:11]=1F)#[N:9].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:8]([C:10]1[C:15]2=[CH:14][C:13]([C:16]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)([C:17]3[NH+:18]([CH3:22])[CH:19]=[N:20][CH:21]=3)[NH2+:30][CH2:31][CH2:32][CH2:33][NH:34][S:35](=[O:37])(=[O:36])[C:38]3[CH:39]=[C:40]([O:44]2)[CH:41]=[CH:42][CH:43]=3)=[CH:12][CH:11]=1)#[N:9]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 18629443HCID 18629443, compound

Product 1

HCID 18629434HCID 18629434, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-{[1-(4-Cyano-3-fluoro-phenyl)-1-(4-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-methyl]-amino}-propyl)-3-hydroxy-benzenesulfonamide trifluoroacetate salt (0.105 g, 0.137 mmol) was dissolved in DMF (20 mL) and treated with Cs2CO3 (0.223 g, 0.69 mmol). After 3 h at 80° C., the reaction mixture was concentrated in vacuo, dissolved in H2O: 0.1% TFA (3 mL), purified by RP LC on a Delta PrepPak eluting with 95:5 to 5:95 H2O(0.1%TFA): CH3CN(0.1%TFA) and lyophilized to give the title compound. MS (M+1) 518.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in H2O
  3. custom0.1% TFA (3 mL), purified by RP LC on a Delta PrepPak
  4. washeluting with 95:5 to 5:95 H2O(0.1%TFA)

Sources & evidence

ORD record
ord-8ab57eb73c70455792adcfa3a8488569
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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