Sodium Bicarbonate → 1-Boc-4-[3-[(2-fluoro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxy}-piperidine

HRID 238421Notes

Reaction equation

HRID 238421 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([NH2:25])[CH:16]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])(O)=O.[Na+].[F:31][C:32]1[C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=[CH:34][N:33]=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([NH:25][C:38]([C:37]3[C:32]([F:31])=[N:33][CH:34]=[CH:35][CH:36]=3)=[O:39])[CH:16]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 219594191-Boc-4-(3-amino-5-trifluoromethyl-phenoxy)piperidineHCID 219595822-Fluoropyridine-3-carbonyl chloride

Product 1

HCID 219595211-Boc-4-[3-[(2-fluoro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxy}-piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Boc-4-(3-amino-5-trifluoromethyl-phenoxy)-piperidine (4.37 g) was dissolved in CH2Cl2 (100 ml) and NaHCO3 (2.4 g, Baker) was added. 2-Fluoropyridine-3-carbonyl chloride (2.12 g) was added an the reaction was stirred at RT for 2.5 h. The reaction was filtered and concentrated in vacuo to yield a yellow foam. (30%) EtOAc/Hexane was added and 1-Boc-4-{3-[(2-fluoro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxy}-piperidine precipitated as an off white solid.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customto yield a yellow foam
  4. custom1-Boc-4-{3-[(2-fluoro-pyridine-3-carbonyl)-amino]-5-trifluoromethyl-phenoxy}-piperidine precipitated as an off white solid

Sources & evidence

ORD record
ord-daa1daa60f874f53a8a84e2752636b6b
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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