Triethylamine → HCID 178456926、化合物

HRID 1620516ノート

反応式

HRID 1620516 の反応式
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6](/[CH:9]=[C:10]2/[C:11]([NH:16][CH2:17][C:18]#[CH:19])=[N:12][C:13](=[O:15])[S:14]/2)[CH2:5][CH2:4]1.[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.O>[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:3]2[CH2:8][CH2:7][CH:6](/[CH:9]=[C:10]3/[C:11]([NH:16][CH2:17][C:18]#[CH:19])=[N:12][C:13](=[O:15])[S:14]/3)[CH2:5][CH2:4]2)=[C:23]([C:29]([F:30])([F:31])[F:32])[CH:22]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 27790174-Chloro-2-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178456897HCID 178456897、化合物

生成物 1

HCID 178456926HCID 178456926、化合物収率 75.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (5Z)-5-(piperidin-4-ylmethylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one dihydrochloride (1.00 g) in DMF (15.5 mL) were added 4-chloro-2-(trifluoromethyl)benzaldehyde (1.10 g) and triethylamine (1.95 mL). The reaction mixture was stirred at room temperature for 1.5 hr, and sodium triacetoxyborohydride (2.28 g) was added. The reaction mixture was stirred at room temperature for 1 hr, poured into water, 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/hexane) to give the title compound (1.04 g).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-f21304f6cb9b4256a26f64266dc1bcdd
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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