Hydrochloric Acid → HCID 25167123、化合物

HRID 1177899ノート

反応式

HRID 1177899 の反応式
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

参加物

9

反応物 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

生成物 1

HCID 25167123HCID 25167123、化合物収率 19.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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 (

出典と根拠

ORDレコード
ord-8a3a96530a6e4ce587d02d4419f3439f
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

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