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Trifluoroacetic acid → HCID 135975008, compound

HRID 2075763
Notes
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Reaction equation

HRID 2075763 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:73])[NH:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]#[C:56][C:57]2[C:58]([C:65]3[CH:70]=[C:69]([Cl:71])[CH:68]=[CH:67][C:66]=3[OH:72])=[N:59][N:60]([CH2:62][CH2:63][OH:64])[CH:61]=2)=[CH:51][CH:50]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:71][C:69]1[CH:68]=[CH:67][C:66]([OH:72])=[C:65]([C:58]2[C:57]([C:56]#[C:55][C:52]3[CH:53]=[CH:54][C:49]([NH:48][C:47]([CH:42]4[CH2:43][O:44][CH2:45][CH2:46][NH:41]4)=[O:73])=[CH:50][CH:51]=3)=[CH:61][N:60]([CH2:62][CH2:63][OH:64])[N:59]=2)[CH:70]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 1359749113(R,S)-{4-[3-(5-Chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenylcarbamoyl}-morpholine-4-carboxylic acid tert-butyl esterHCID 135974922Piperidine-2(R)-carboxylic acid {4-[3-(5-chloro-2-hydroxy-phenyl)-1-(2-hydroxy-ethyl)-1H-pyrazol-4-ylethynyl]-phenyl}-amide

Product 1

HCID 135975008HCID 135975008, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the same procedure for the preparation of 5A, treatment of compound 16A (870 mg) with TFA (10 mL) in methylene chloride (10 mL) gives compound 17A in 74.0% yield. 1H NMR (DMSO-d6, 500 MHz) δ 10.67 (s, 1H), 10.02 (s, 1H), 8.35 (s, 1H), 8.28 (s, 1H), 7.73 (d, 2H, J=8.0 Hz), 7.47 (d, 2H, J=8.5 Hz), 7.30 (d, 1H, J=9.0 Hz), 6.99 (d, 1H, J=8.5 Hz), 5.01 (br s, 1H), 4.26 (br s, 2H), 3.83 (d, 1H, J=7.5 Hz), 3.78 (d, 2H, J=2.5 Hz), 3.61 (m, 3H), 3.52 (m, 2H), 3.43 (t, 1H, J=10.0 Hz), 2.85 (d, 1H, J=13.0 Hz), 2.75 (t, 1H, J=11.0 Hz). LCMS (ESI) m/z 467.09 (MH+, 100); HPLC: tR=3.92 min.

Sources & evidence

ORD record
ord-184fa3081a62431e993b4b23a294afd3
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07923004B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes