1-Hydroxybenzotriazole → HCID 178482472、化合物

HRID 1620469ノート

反応式

HRID 1620469 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[CH3:42][NH:43][C:44]1=[N:45][C:46](=[O:56])[S:47]/[C:48]/1=[CH:49]\[CH:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>CN(C)C=O.O.C(N(CC)CC)C>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:53]1[CH2:54][CH2:55][CH:50](/[CH:49]=[C:48]2/[C:44]([NH:43][CH3:42])=[N:45][C:46](=[O:56])[S:47]/2)[CH2:51][CH2:52]1)=[O:7]

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 1417522,4-Bis(trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178482469HCID 178482469、化合物

生成物 1

HCID 178482472HCID 178482472、化合物収率 56.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 2,4-bis(trifluoromethyl)benzoic acid (83 mg) in N,N-dimethylformamide (6 mL) were added 1-hydroxybenzotriazole (123 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (154 mg), and the mixture was stirred for 5 min under ice-cooling. To the reaction mixture were added triethylamine (0.2 mL) and (5Z)-4-(methylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) under ice-cooling, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate/pentane to give the title compound (85 mg).

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  9. customrecrystallized from ethyl acetate/pentane

出典と根拠

ORDレコード
ord-ace52515df45495d972d3bb4af8b426c
出典データセット
uspto-grants-2014_07
特許番号
US08772277B2

反応ノート

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