Trifluoroacetic acid → HCID 66673508, compound

HRID 423699Notes

Reaction equation

HRID 423699 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][C:15]([O:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)=[CH:14][CH:13]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH3:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24995277HCID 24995277, compound

Product 1

HCID 66673508HCID 66673508, compoundYield 136%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 4-[({6-[2-methyl-4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (Example 185, 57 mg, 0.124 mmol), TFA (0.095 mL, 1.24 mmol) in CH2Cl2 (3 mL) was stirred at ambient temperature for 3 h. The mixture was concentrated to give (80 mg, quantitative yield) of 2-[2-methyl-4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine trifluoroacetate as a clear oil. 1H NMR (400 MHz, CDCl3): δ 8.78 (d, 1H, J=2.0 Hz), 7.97-7.83 (m, 3H), 7.69 (d, 1H, J=8.7 Hz), 7.58-7.48 (m, 1H), 4.17 (d, 2H, J=5.5 Hz), 3.70-3.55 (m, 2H), 3.14-3.01 (m, 5H), 2.39 (s, 3H), 2.34-2.21 (m, 2H), 2.25-2.10 (m, 2H), 1.97-1.83 (m, 2H); LRMS (ESI), m/z 361 (M+H).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-76b9b8be33ff4bab9566247613542eda
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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