Hexane → HCID 66976947, compound

HRID 712221Notes

Reaction equation

HRID 712221 reaction equation
Cl.[F:2][C:3]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH3:12][CH2:13]N(C(C)C)C(C)C.[Br:21][C:22]1[CH:23]=[N:24][C:25](Cl)=[N:26][CH:27]=1.CCCCCC>CCO>[Br:21][C:22]1[CH:23]=[N:24][C:25]([N:6]2[CH2:7][CH2:8][C:3]([F:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:5]2)=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 533932674-Fluoropiperidine-4-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 66976947HCID 66976947, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-fluoropiperidine-4-carboxylate hydrochloride (0.70 g, 4.34 mmol) in EtOH (10.0 mL) was added DIPEA (1.92 mL, 10.86 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.70 g, 3.62 mmol). The reaction was then heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 3.0% EtOAc:hexane to obtain the desired product as a yellow solid (0.50 g, 42% yield). MS: 332.12 [M+H]+.

Workup

  1. temperatureThe reaction was then heated up to 70° C. for 1 h
  2. customAfter completion of reaction (by TLC), solvent
  3. customwas evaporated
  4. customthe crude residue purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-68c028a1ec804e348b127ea7b18de2f1
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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