Dimethylformamide dimethyl acetal → 5-[2-(3-Nitrophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile

HRID 478191

反応式

HRID 478191 の反応式
[CH:1]1([C:7]2[C:8]([C:22]#[N:23])=[C:9]([S:20][CH3:21])[S:10][C:11]=2[C:12](=O)[C:13]([CH3:18])=[CH:14]N(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(OC)OC)C.[N+:32]([C:35]1[CH:36]=[C:37]([NH:41][C:42]([NH2:44])=[NH:43])[CH:38]=[CH:39][CH:40]=1)([O-:34])=[O:33]>C1(C)C=CC=CC=1.CCOC(C)=O.CN(C=O)C>[N+:32]([C:35]1[CH:36]=[C:37]([NH:41][C:42]2[N:44]=[C:12]([C:11]3[S:10][C:9]([S:20][CH3:21])=[C:8]([C:22]#[N:23])[C:7]=3[CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:13]([CH3:18])=[CH:14][N:43]=2)[CH:38]=[CH:39][CH:40]=1)([O-:34])=[O:33]

参加物

7

反応物 3

HCID 78373Dimethylformamide dimethyl acetalHCID 695552744-Cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrileHCID 178418758HCID 178418758、化合物

生成物 1

HCID 220190285-[2-(3-Nitrophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile収率 42%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of 4-cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrile (0.5 g, 1.7 mmol) in toluene (3 ml) was added DMF-DMA and the reaction was heated at 90° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The crude product was combined with DMF (10 ml) and 3-Nitrophenylguanidine (0.5 g, 2.78 mmol) in a sealed tube and heated at 120° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The reaction was partitioned between EtOAc and water, the organics were dried over sodium sulfate then concentrated in vacuo. The crude product was purified by chromatography (silica gel, 10% EtOAC:hexanes) to afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps. 1H NMR (CDCl3) δ1.0-2.0 (m, 10H), 2.1 (s, 3H), 2.6(s, 3H), 7.4(m, 1H), 7.7 (d, 1H), 7.8 (d, 1H), 8.3 (s, 1H), 8.7 (s, 1H).

後処理

  1. customresulting in conversion to product
  2. temperatureheated at 120° C. overnight
  3. customresulting in conversion to product
  4. customThe reaction was partitioned between EtOAc and water
  5. dry with materialthe organics were dried over sodium sulfate
  6. concentrationthen concentrated in vacuo
  7. customThe crude product was purified by chromatography (silica gel, 10% EtOAC:hexanes)
  8. customto afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps

出典と根拠

ORDレコード
ord-6b13f0f56ddc4635806ba795084de9b6
出典データセット
uspto-grants-2003_11
特許番号
US06642227B2

関連ノート

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