Hydrochloric Acid → HCID 25167123, 화합물

HRID 1177899노트

반응식

HRID 1177899 반응식
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[O:15][C:14]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)=[N:13][N:12]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:46][CH2:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:52][CH2:51]1)=[O:49].Cl>CN(C=O)C.O>[CH3:10][C:11]1[O:15][C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([NH:46][CH2:47][C:48](=[O:49])[N:50]3[CH2:51][CH2:52][N:53]([C:56](=[O:67])[C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=4[C:63]([F:64])([F:66])[F:65])[CH2:54][CH2:55]3)=[O:22])=[CH:23][CH:24]=2)=[N:13][N:12]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 177237644-(5-Methyl-1,3,4-oxadiazol-2-yl)benzoic acidHCID 595596292-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone

생성물 1

HCID 25167123HCID 25167123, 화합물수율 19.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (180 mg, 0.24 mL, 1.4 mmol) was added drop wise to 4-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzoic acid (90 mg, 0.4 mmol) in DMF (3 mL). EDCI (92 mg, 0.48 mmol) and HOBT (65 mg, 0.48 mmol) were added consecutively and, after 10 minutes, 2-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone in its HCl salt form (150 mg, 0.4 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue purified by column chromatography (using silica gel of 60-120 mesh and 10% EtOAc in Hexane as eluent to afford 40 mg (19.9% yield) of 4-(5-Methyl-[1,3,4]oxadiazol-2-yl)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 96.6%. 1H NMR (CDCl3): δ 8.1 (d, 2H), 7.9 (m, 2H), 7.7 (m, 1H), 7.5 (m, 2H), 7.3 (m, 2H), 4.2 (m, 2H), 4.0 (m, 2H), 3.6 (m, 3H), 3.4 (m, 1H), 2.6 (s, 3H).

후처리

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. custompurified by column chromatography (

출처 및 근거

ORD 기록
ord-8a3a96530a6e4ce587d02d4419f3439f
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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