Trifluoroacetic acid → 1-Methylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423525Notes

Reaction equation

HRID 423525 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28](C)([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)=[N:9][CH:10]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O.C(N(C(C)C)CC)(C)C.ClC(OC(C)C)=O>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:16]=2)=[N:9][CH:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 249943371,1-Dimethylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

Product 1

HCID 249946481-Methylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (53 mg, 91%) was prepared as an off-white solid from 1,1-dimethylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate (Example 78, 60 mg, 0.13 mmol) and TFA (0.25 mL) in CH2Cl2 (4 mL) then diisopropylethylamine (1.5 ml) and isopropyl chloroformate (1.0M in toluene, 0.16 mL, 0.16 mmol) in a manner similar to Example 74. 1H NMR (400 MHz, CDCl3): δ 9.12 (s, 1H), 8.21 (d, 1H, J=8.3 Hz), 8.04 (d, 2H, J=8.8 Hz), 7.84 (d, 1H, J=8.3 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.92 (septet, 1H, J=6.3 Hz), 4.21 (bs, 2H), 3.88 (d, 2H, J=6.4 Hz), 3.13 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 433 (M+H).

Sources & evidence

ORD record
ord-c5d17c1f4df04ce68e27cf6a55d30f50
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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