Trifluoroacetic acid → Piperidine-2(S)-carboxylic acid {4-[3-(5-chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenyl}-amide

HRID 2075761Notes

Reaction equation

HRID 2075761 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:33])=[C:6]([C:8]2[C:12]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([C@H:24]4[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]4)=[O:23])=[CH:17][CH:16]=3)=[CH:11][N:10]([CH2:30][CH2:31][OH:32])[N:9]=2)[CH:7]=1.C(OC(N1CCCC[C@H]1C(=O)NC1C=CC(C#CC2C(C3C=C(Cl)C=CC=3O)=NN(CCO)C=2)=CC=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:33])=[C:6]([C:8]2[C:12]([C:13]#[C:14][C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22]([C@@H:24]4[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]4)=[O:23])=[CH:19][CH:20]=3)=[CH:11][N:10]([CH2:30][CH2:31][OH:32])[N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 135974922Piperidine-2(R)-carboxylic acid {4-[3-(5-chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenyl}-amideHCID 1359749312(S)-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 135974994Piperidine-2(S)-carboxylic acid {4-[3-(5-chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenyl}-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the same procedure for the preparation of 5A, treatment compound 9A with TFA in methylene chloride to give compound 10A in quantitative yield. Its 1H NMR and LCMS data are identical with those of compound 5A.

Sources & evidence

ORD record
ord-b4c0e11e62ab4c9fbb678989d342cfa7
Source dataset
uspto-grants-2011_04
Patent number
US07923004B2

Reaction notes

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