Water → HCID 23729205, compound

HRID 1911773Notes

Reaction equation

HRID 1911773 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][NH:7][CH2:8][C:9]1[C:10]([N:20]([CH2:23][CH:24]2[CH2:27][CH2:26][CH2:25]2)[CH2:21][CH3:22])=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19].[Br:37][C:38]1[CH:39]=[N:40][C:41](Cl)=[N:42][CH:43]=1.[F-].[K+].O>CN(C)C=O.CCOC(C)=O>[F:36][C:2]([F:35])([F:1])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH2:8][C:9]1[C:10]([N:20]([CH2:23][CH:24]2[CH2:27][CH2:26][CH2:25]2)[CH2:21][CH3:22])=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19])[C:41]1[N:42]=[CH:43][C:38]([Br:37])=[CH:39][N:40]=1

Participants

7

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 6066655-Bromo-2-chloropyrimidineHCID 58795795HCID 58795795, compound

Product 1

HCID 23729205HCID 23729205, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of {3-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-8-methyl-quinolin-2-yl}-cyclobutylmethyl-ethyl-amine (0.23 g, 0.46 mmol), 5-bromo-2-chloropyrimidine (0.09 g, 0.46 mmol), and potassium fluoride (0.11 g, 1.8 mmol) in dimethyl formamide (10 ml) was heated at 80° C. overnight. After cooling the reaction to ambient temperature water (10 mL) and EtOAc (20 mL) were added and stirred for 0.5 h. Thereafter, the organic layer was separated, washed with brine, dried over sodium sulfate, filtered and solvent evaporated in vacuo. The crude was purified by chromatography using silica gel to afford the title compound as a colorless liquid (0.14 g, 47%).

Workup

  1. temperatureAfter cooling
  2. additionwere added
  3. customThereafter, the organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent evaporated in vacuo
  8. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-54b00548465b402d82c45b0b73f25973
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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