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

HRID 2075774Notes

Reaction equation

HRID 2075774 reaction equation
ClC1C=CC(O)=C(C2C(C#CC3C=CC(NC([C@H]4CCCCN4)=O)=CC=3)=CN(CCO)N=2)C=1.C(OC([N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH:42]1[C:47](=[O:71])[NH:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]#[C:56][C:57]2[C:58]([C:63]3[CH:68]=[C:67]([Cl:69])[CH:66]=[CH:65][C:64]=3[OH:70])=[N:59][N:60]([CH3:62])[CH:61]=2)=[CH:51][CH:50]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:69][C:67]1[CH:66]=[CH:65][C:64]([OH:70])=[C:63]([C:58]2[C:57]([C:56]#[C:55][C:52]3[CH:51]=[CH:50][C:49]([NH:48][C:47]([CH:42]4[CH2:43][O:44][CH2:45][CH2:46][NH:41]4)=[O:71])=[CH:54][CH:53]=3)=[CH:61][N:60]([CH3:62])[N:59]=2)[CH:68]=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 1363466873-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-methyl-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 136346686Morpholine-3-carboxylic acid {4-[3-(5-chloro-2-hydroxy-phenyl)-1-methyl-1H-pyrazol-4-ylethynyl]-phenyl}-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the same procedure for the preparation of compound 5A, treatment of compound 6D with TFA in methylene chloride gives the title compound 7D as a white powder in similar yield. LCMS (ESI) m/z 437.28 (MH+, 100); HPLC: tR=4.15 min.

Sources & evidence

ORD record
ord-d9383c3f2d3543cf877bb93ef1fb1874
Source dataset
uspto-grants-2011_04
Patent number
US07923004B2

Reaction notes

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