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

HRID 423570Notes

Reaction equation

HRID 423570 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N: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][N:12]=2)=[CH:7][CH:6]=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:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][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:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 591778161,1-Dimethylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylate

Product 1

HCID 249934061-Methylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (80 mg, 92%) was prepared as a white solid from 1,1-dimethylethyl 4-[({2-[4-(methylsulfonyl)phenyl]-5-pyrimidinyl}oxy)methyl]-1-piperidinecarboxylate (Example 128, 90 mg, 0.20 mmol) and TFA (1.0 mL) in CH2Cl2 (6 mL) then diisopropylethylamine (1.0 ml) and isopropyl chloroformate (1.0M in toluene, 0.22 mL, 0.22 mmol) in a manner similar to Example 74. 1H NMR (400 MHz, CDCl3): δ 8.56 (d, 2H, J=8.5 Hz), 8.48 (s, 2H), 8.02 (d, 2H, J=8.6 Hz), 4.92 (septet, 1H, J=6.2 Hz), 4.24 (bs, 2H), 3.97 (d, 2H, J=6.3 Hz), 3.08 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (APCI), m/z 434 (M+H).

Sources & evidence

ORD record
ord-940853c48ebf4c878ba1b32dfedd3464
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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