Potassium Carbonate → HCID 86670965, compound

HRID 515332Notes

Reaction equation

HRID 515332 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:23])[NH:7][C:8]2[CH:22]=[CH:21][C:11]([C:12]([N:14]([CH3:20])[CH:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([OH:41])([C:37]([F:40])([F:39])[F:38])[C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]1([CH2:4][NH:5][C:6](=[O:23])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:14]([CH:15]3[CH2:19][CH2:18][N:17]([CH2:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]([OH:41])([C:33]([F:34])([F:35])[F:36])[C:37]([F:38])([F:39])[F:40])=[CH:30][CH:31]=4)[CH2:16]3)[CH3:20])=[O:13])=[CH:21][CH:22]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67191476HCID 67191476, compound

Product 1

HCID 86670965HCID 86670965, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(3-(cyclopropylmethyl)ureido)-N-methyl-N-(pyrrolidin-3-yl)benzamide (4.74 mmol, 1.5 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (4.74 mmol, 1.598 g) and potassium carbonate (7.11 mmol, 0.983 g) in acetonitrile (40 mL) was refluxed for 5 hours. The reaction was concentrated under reduced pressure and dichloromethane/methanol was added. The suspension was filtered and the filtrate was concentrated under reduced pressure. Chromatography on silica eluting with a gradient of dichloromethane/methanol gave the title compound (400 mg). MS (ESI) m/z 573.2 [M+H]+

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe reaction was concentrated under reduced pressure and dichloromethane/methanol
  3. additionwas added
  4. filtrationThe suspension was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5957df4ca8114907a22e2c62da29ce2c
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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