Trifluoroacetic acid → HCID 58025821, 화합물

HRID 1046943노트

반응식

HRID 1046943 반응식
C(O[C:6]([NH:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]([CH3:18])=[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.CCN(C(C)C)C(C)C.[F:53][CH:54]([F:64])[O:55][C:56]1[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=1[CH:58]=O.[F:65][C:66]1[CH:74]=[C:73]([F:75])[CH:72]=[C:71]([F:76])[C:67]=1C(Cl)=O>C(Cl)Cl>[F:53][CH:54]([F:64])[O:55][C:56]1[CH:63]=[CH:62][CH:61]=[CH:60][C:57]=1[CH:58]1[N:8]([C:6]([C:67]2[C:66]([F:65])=[CH:74][C:73]([F:75])=[CH:72][C:71]=2[F:76])=[O:7])[N:9]=[C:10]([C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[S:11]1

참가 물질

8

반응물 6

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 27369842-(Difluoromethoxy)benzaldehydeHCID 67279032tert-Butyl 2-(4-fluorobenzoyl)hydrazine-1-carboxylateHCID 86637598HCID 86637598, 화합물

생성물 1

HCID 58025821HCID 58025821, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N′-(6-Methyl-pyridine-3-carbothioyl)-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 (0.287 mmol) is added to the solution and the mixture is treated with 2-difluoromethoxy-benzaldehyde (0.12 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 ambient temperature for 16 hours and purified by preparative HPLC (20-100% MeCN/H2O) to yield [2-(2-difluoromethoxy-phenyl)-5-(6-methyl-pyridin-3-yl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone: 1H NMR (400 MHz, CDCl3) 8.71 (d, J=2.1 Hz, 1H), 7.81 (dd, J1=8.2 Hz, J2=2.2 Hz, 1H), 7.53 (s, 1H), 7.36-7.4 (m, 2H), 7.26 (d, J=8.1 Hz, 2H), 7.18 (d, J=8.3 Hz, 1H), 6.78 (t, J=8.3 Hz, 2H), 6.67 (dd, J1=75.0 Hz, J2=71.7 Hz, 1H), 2.64 (s, 3H); LC/MS (ES+): (M+1) 480.1.

후처리

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

출처 및 근거

ORD 기록
ord-877c62aef0df40468ee919ee45fabe54
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569345B2

반응 노트

불러오는 중…