Triethylamine → HCID 58547336, compound

HRID 1850282Notes

Reaction equation

HRID 1850282 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:17](Br)=[CH:16][C:15]([F:19])=[CH:14][N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:20]1[CH2:25][CH2:24][CH:23]([CH2:26][OH:27])[CH2:22][CH2:21]1.CCN(CC)CC>CS(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:17]([N:20]3[CH2:25][CH2:24][CH:23]([CH2:26][OH:27])[CH2:22][CH2:21]3)=[CH:16][C:15]([F:19])=[CH:14][N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 58546726HCID 58546726, compound

Product 1

HCID 58547336HCID 58547336, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(3-bromo-5-fluoro-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (58) (660 mg, 2 mmol, Preparation 17) and piperidin-4-yl-methanol (35) (230 mg, 2 mmol) in DMSO (20 mL) was added Et3N (404 mg, 4 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (50 mL×3). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography (EtOAc:PE=3:1) on silica gel to give (76) (490 mg, 1.34 mmol, yield 67%). ESI-MS (M+1): 366 calc. for C19H28FN3O3 365.

Workup

  1. extractionextracted with EtOAc (50 mL×3)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography (EtOAc:PE=3:1) on silica gel

Sources & evidence

ORD record
ord-1d84d25cdfbc4b26b45a286ba04eb2e0
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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