Diisopropylethylamine → (2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethanone
반응식
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[I-].[CH2:49]([N+:53]1[N:57]=[C:56]([CH3:58])[S:55][C:54]=1[CH3:59])[CH2:50][CH2:51][CH3:52]>>[CH2:49]([N:53]1[N:57]=[C:56]([CH3:58])[S:55]/[C:54]/1=[CH:59]\[C:4]([C:3]1[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:2]=1[F:1])=[O:6])[CH2:50][CH2:51][CH3:52]참가 물질
반응물 4
생성물 1
실험 절차
In a 20 mL vial 2-fluoro-5-(trifluoromethyl)benzoic acid (0.9 mL of 0.2 M in DMA, 1.10 equiv) was added followed by the addition of HATU (76 mg in 0.7 mL of DMA, 0.2 mmol, 1.20 equiv.), DIEA (51 mg in 0.7 mL of DMA, 0.4 mmol, 2.40 equiv.), and finally 3-butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide (49 mg in 0.7 mL of DMA, 0.17 mmol, 1 equiv.). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.92 (t, 3 H) 1.26-1.37 (m, 2 H) 1.72-1.79 (m, 2 H) 2.50 (s, 3 H) 4.19 (t, 2 H) 6.47 (s, 1 H) 7.50-7.58 (m, 1 H) 7.87-7.93 (m, 1 H) 8.09-8.12 (m, 1 H); MS (ESI) m/z 361 (M+H)+.
후처리
- concentrationconcentrated in vacuo
- custompurified by reverse phase HPLC
출처 및 근거
- ORD 기록
- ord-6e2b633d11474b4a8d1e2ab5d9a93cd6
- 출처 데이터셋
- uspto-grants-2013_07
- 특허 번호
- US08481574B2
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