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

HRID 478191
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HRID 478191 반응식
[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]
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 1140
Toluene
용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매2회

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온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6b13f0f56ddc4635806ba795084de9b6
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06642227B2

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