Trifluoroacetic acid → HCID 67279381, compound

HRID 1694368Notes

Reaction equation

HRID 1694368 reaction equation
C(O[C:6]([NH:8][NH:9][C:10](=[S:19])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1)=[O:7])(C)(C)C.C(OC(NNC(=O)C1C=CC(F)=CC=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[CH3:54][O:55][C:56](=[O:74])[C:57]1[CH:62]=[CH:61][CH:60]=[C:59]([C:63]2[O:64][C:65]3[CH:71]=[CH:70][CH:69]=[C:68]([CH:72]=O)[C:66]=3[N:67]=2)[CH:58]=1.[F:75][C:76]1[CH:84]=[C:83]([F:85])[CH:82]=[C:81]([F:86])[C:77]=1C(Cl)=O>C(Cl)Cl>[CH3:54][O:55][C:56](=[O:74])[C:57]1[CH:62]=[CH:61][CH:60]=[C:59]([C:63]2[O:64][C:65]3[CH:71]=[CH:70][CH:69]=[C:68]([CH:72]4[N:8]([C:6](=[O:7])[C:77]5[C:76]([F:75])=[CH:84][C:83]([F:85])=[CH:82][C:81]=5[F:86])[N:9]=[C:10]([C:11]5[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=5)[S:19]4)[C:66]=3[N:67]=2)[CH:58]=1

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 67279032tert-Butyl 2-(4-fluorobenzoyl)hydrazine-1-carboxylateHCID 860661063-(4-Formyl-benzooxazol-2-yl)-benzoic acid methyl esterHCID 86637600HCID 86637600, compound

Product 1

HCID 67279381HCID 67279381, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N′-(3,4-Difluoro-thiobenzoyl)-hydrazinecarboxylic acid tert-butyl ester (0.1 mmol) prepared as described in example 3 for N′-(4-fluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester, is treated with TFA (1 mmol) in dry CH2Cl2 (1 mL) at room temperature for 30 minutes. Solvent is removed and the residue is dissolved in dry CH2Cl2 (1 mL). DIEA (0.57 mmol) is added to the solution and the mixture is treated with 3-(4-formyl-benzooxazol-2-yl)-benzoic acid methyl ester (0.064 mmol) in the presence of 4 Å molecular sieves. 2,4,6-Trifluorobenzoyl chloride (0.15 mmol) is added after 5 minutes. The mixture is kept at room temperature for 16 hours and purified by preparative HPLC (20-100% MeCN/H2O) to yield 3-{4-[5-(3,4-difluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-benzooxazol-2-yl}-benzoic acid methyl ester. LC/MS (ES+): (M+1) 610.0, (M+Na) 632.0.

Workup

  1. customSolvent is removed
  2. dissolutionthe residue is dissolved in dry CH2Cl2 (1 mL)
  3. custompurified by preparative HPLC (20-100% MeCN/H2O)

Sources & evidence

ORD record
ord-0dc35773e7c84753927ee127f3492fc4
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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