Potassium Carbonate → HCID 59175878, compound

HRID 1807750Notes

Reaction equation

HRID 1807750 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[F:19][C:20]1[CH:25]=[C:24]([C:26]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[O:27])[CH:23]=[CH:22][C:21]=1[NH:34][C:35](=[O:44])[NH:36][CH2:37][C:38]1([C:41]([NH2:43])=[O:42])[CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:19][C:20]1[CH:25]=[C:24]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([C:9]([OH:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=3)[CH2:30][CH2:29]2)=[O:27])[CH:23]=[CH:22][C:21]=1[NH:34][C:35](=[O:44])[NH:36][CH2:37][C:38]1([C:41]([NH2:43])=[O:42])[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 59175911HCID 59175911, compound

Product 1

HCID 59175878HCID 59175878, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.303 mmol, 102 mg), 1-((3-(2-fluoro-4-(piperazine-1-carbonyl)phenyl)ureido)methyl)cyclopropanecarboxamide (0.303 mmol, 110 mg) and potassium carbonate (0.303 mmol, 42 mg) were stirred in acetonitrile (2 ml) at room temperature for 4 hours. The reaction was concentrated under reduced pressure and the residue obtained was purified by silica chromatography eluting with dichloromethane increasing to dichloromethane:methanol (10%). Further purification by HPLC and SCX chromatography yielded the title compound (18 mg). MS (ESI) m/z 620.7 [M+H]+

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue obtained
  3. customwas purified by silica chromatography
  4. washeluting with dichloromethane increasing to dichloromethane
  5. customFurther purification by HPLC and SCX chromatography

Sources & evidence

ORD record
ord-7b459196eab54fddbcee72b4275146c2
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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