1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678444ノート

反応式

HRID 1678444 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)[N:3]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH2:28].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]([NH:28][CH2:27][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20]([F:19])([F:29])[F:30])=[O:18])[CH2:14][CH2:15]2)[N:3]=1

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 764472-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 866443161-[4-Chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid

生成物 1

HCID 866443121-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide収率 88.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (885 mg, 3.25 mmol, 1.00 equiv) in DMF (32 ml) at room temperature, {[2-(trifluoromethyl)phenyl]methyl}amine (456 μL, 3.25 mmol, 1.00 equiv), EDCI (748 mg, 3.90 mmol, 1.20 equiv), HOBT (527 mg, 3.90 mmol, 1.00 equiv), and diisopropylethylamine (DIEA, 2.80 ml, 16.3 mmol, 5.00 equiv) were added. Stirring was continued overnight at room temperature. The reaction mixture was partitioned between 1:1 water and ethyl acetate (200 ml). The product was extracted three times with ethyl acetate (50 ml). The ethyl acetate extracts were combined and washed successively with saturated ammonium chloride (100 ml), water (100 ml), and saturated sodium chloride (100 ml). The ethyl acetate solution was dried with Na2SO4, filtered, and concentrated under reduced pressure to yield 1.23 g (88%) of the title compound. MS ES+): m/e 428.7 [M+H]+.

後処理

  1. customThe reaction mixture was partitioned between 1:1 water and ethyl acetate (200 ml)
  2. extractionThe product was extracted three times with ethyl acetate (50 ml)
  3. washwashed successively with saturated ammonium chloride (100 ml), water (100 ml), and saturated sodium chloride (100 ml)
  4. dry with materialThe ethyl acetate solution was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a4ad8a7b02234045aa988221837ad5a8
出典データセット
uspto-grants-2011_08
特許番号
US08008483B2

反応ノート

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