Trifluoroacetic acid → HCID 58025839, 화합물

HRID 1046945노트

반응식

HRID 1046945 반응식
C(O[C:6]([NH:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([F:18])=[CH:16][CH:17]=1)=[S:11])=[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.C1(SC)C=CC=CC=1.CCN(C(C)C)C(C)C.[F:61][CH:62]([F:72])[O:63][C:64]1[CH:71]=[CH:70][CH:69]=[CH:68][C:65]=1[CH:66]=O.[F:73][C:74]1[CH:82]=[C:81]([F:83])[CH:80]=[C:79]([F:84])[C:75]=1C(Cl)=O>C(Cl)Cl>[F:61][CH:62]([F:72])[O:63][C:64]1[CH:71]=[CH:70][CH:69]=[CH:68][C:65]=1[CH:66]1[N:8]([C:6]([C:75]2[C:74]([F:73])=[CH:82][C:81]([F:83])=[CH:80][C:79]=2[F:84])=[O:7])[N:9]=[C:10]([C:12]2[CH:13]=[N:14][C:15]([F:18])=[CH:16][CH:17]=2)[S:11]1

참가 물질

9

반응물 7

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 81531DiisopropylethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 27369842-(Difluoromethoxy)benzaldehydeHCID 67279032tert-Butyl 2-(4-fluorobenzoyl)hydrazine-1-carboxylateHCID 86637599HCID 86637599, 화합물

생성물 1

HCID 58025839HCID 58025839, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N′-(6-fluoro-pyridine-3-carbothioyl)-hydrazinecarboxylic acid tert-butyl ester (0.044 mmol) prepared as described in example 3 for N′-(4-fluoro-benzoyl)-hydrazinecarboxylic acid tert-butyl ester, is treated with TFA (0.44 mmol) and thioanisole (0.44 mmol) in dry CH2Cl2 (1 mL) at room temperature for 30 minutes. The solvent is removed and the residue is dissolved in dry CH2Cl2 (1 mL). DIEA (0.22 mmol) is added to the solution and the mixture is treated with 2-difluoromethoxy-benzaldehyde (0.067 mmol) in the presence of 4 Å molecular sieves. 2,4,6-Trifluorobenzoyl chloride (0.089 mmol) is added after 5 minutes. The mixture is kept at room temperature for 16 hours and purified by preparative silica gel TLC (30% EtOAc/hexane) to yield [2-(2-difluoromethoxy-phenyl)-5-(6-fluoro-pyridin-3-yl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone: 1H NMR (400 MHz, CDCl3) 8.39 (s, 1H), 7.93-7.97 (m, 1H), 7.54 (s, 1H), 7.37-7.41 (m, 2H), 7.24-7.27 (m, 1H), 7.19 (d, J=8.1 Hz, 1H), 6.97 (dd, J1=8.6 Hz, J2=2.7 Hz, 1H), 6.78 (t, J=8.3 Hz, 2H), 6.67 (dd, J1=75.0 Hz, J2=71.7 Hz, 1H); LC/MS (ES+): (M+1) 484.1.

후처리

  1. customThe solvent is removed
  2. dissolutionthe residue is dissolved in dry CH2Cl2 (1 mL)
  3. custompurified by preparative silica gel TLC (30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-bbdbb2a885d84255b50a3f93f043ce2f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569345B2

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