Dimethylformamide → 3-(4-(4-(3,4-Dimethyl-phenyl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamide

HRID 522884ノート

反応式

HRID 522884 の反応式
ClC1N=C(Cl)N=CN=1.CN(C=O)C.C(N(C(C)C)C(C)C)C.NC1C(C)=C(C=CC=1)C(N)=O.Cl[C:35]1[N:40]=[CH:39][N:38]=[C:37]([NH:41][C:42]2[C:43]([CH3:51])=[C:44]([CH:48]=[CH:49][CH:50]=2)[C:45]([NH2:47])=[O:46])[N:36]=1.[CH3:52][C:53]1[CH:54]=[C:55]([N:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)[CH:56]=[CH:57][C:58]=1[CH3:59]>O>[CH3:52][C:53]1[CH:54]=[C:55]([N:60]2[CH2:61][CH2:62][N:63]([C:35]3[N:40]=[CH:39][N:38]=[C:37]([NH:41][C:42]4[C:43]([CH3:51])=[C:44]([CH:48]=[CH:49][CH:50]=4)[C:45]([NH2:47])=[O:46])[N:36]=3)[CH2:64][CH2:65]2)[CH:56]=[CH:57][C:58]=1[CH3:59]

参加物

8

反応物 6

HCID 6228DimethylformamideHCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 27237821-(3,4-Xylyl)piperazineHCID 164957733-Amino-2-methylbenzamideHCID 866852463-(4-Chloro-1,3,5-triazin-2-ylamino)-2-methylbenzamide

生成物 1

HCID 673757313-(4-(4-(3,4-Dimethyl-phenyl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamide収率 56%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2,4-dichloro-1,3,5-triazine (50.0 mg, 0.333 mmol) in DMF (1334 μL, 0.333 mmol) was added N-ethyl-N-isopropylpropan-2-amine (174 μL, 1.000 mmol). The reaction mixture was cooled in an ice-water bath prior to the addition of 3-amino-2-methylbenzamide (50.1 mg, 0.333 mmol). The reaction mixture was stirred for 1 h at 0° C. at which time LC-MS revealed complete conversion to 3-(4-chloro-1,3,5-triazin-2-ylamino)-2-methylbenzamide. To this yellow solution was added 1-(3,4-dimethylphenyl)piperazine (63.4 mg, 0.333 mmol). The reaction mixture was allowed to stir and warm slowly to RT over 3 h. Water was added yielding a precipitate, which was filtered off, washed with water, and then purified further by reverse phase liquid chromatography using TFA as a modifier. Fractions containing the product were combined and washed with sat. NaHCO3. The product was extracted with CH2Cl2. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated to afford 3-(4-(4-(3,4-dimethyl-phenyl)piperazin-1-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamide (78 mg, 0.187 mmol, 56.0% yield) was obtained as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. stirringto stir
  3. temperaturewarm slowly to RT over 3 h
  4. customyielding a precipitate, which
  5. filtrationwas filtered off
  6. washwashed with water
  7. custompurified further by reverse phase liquid chromatography
  8. additionFractions containing the product
  9. washwashed with sat. NaHCO3
  10. extractionThe product was extracted with CH2Cl2
  11. washThe organic phase was washed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated

出典と根拠

ORDレコード
ord-64143ab4d2c042caa894239489221090
出典データセット
uspto-grants-2016_05
特許番号
US09334269B2

反応ノート

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