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Ethylenediamine → HCID 11235910, 화합물

HRID 2216316
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HRID 2216316 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.[CH2:29](N)[CH2:30][NH2:31].CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[NH:26]1[CH2:29][CH2:30][N:31]=[C:25]1[C:24]1[CH:23]=[CH:22][C:21]([S:18]([C:5]2[C:6]([NH:8][C:9]3[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=3[CH3:15])=[N:7][C:2]([CH3:1])=[N:3][CH:4]=2)(=[O:20])=[O:19])=[CH:28][CH:27]=1
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반응물 4

HCID 3301EthylenediamineHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11749692HCID 11749692, 화합물

생성물 1

HCID 11235910HCID 11235910, 화합물수율 15.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 4-[2-methyl-4-(2,4,6-trimethyl-phenylamino)-pyrimidine-5-sulfonyl]-benzonitrile (83 mg, 0.21 mmol), prepared by the method described in Example 22, ethylenediamine (0.042 mL, 0.63 mmol), p-TsOH.H2O (59 mg, 0.31 mmol) and toluene (4 mL) was heated at reflux under N2 overnight and then cooled to room temperature. Saturated aqueous NaHCO3 was added, and the mixture was extracted three times with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (75:25 EtOAc/MeOH) to provide the target compound (14 mg, 15%) as a white solid: mp 240–242° C.; 1H NMR (300 MHz, CDCl3) δ 8.78 (s, 1H), 8.27 (br s, 1H), 8.00 (d, J=8.5 Hz, 2H), 7.95 (d, J=8.5 Hz, 2H), 6.92 (s, 2H), 4.80 (br s, 1H), 3.83 (s, 4H), 2.40 (s, 3H), 2.30 (s, 3H), 2.01 (s, 6H); ESI MS m/z 436 [(M+H)+, calcd for C23H26N5O2S, 436.2].

후처리

  1. customprepared by the method
  2. temperaturewas heated
  3. temperatureat reflux under N2 overnight
  4. extractionthe mixture was extracted three times with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (75:25 EtOAc/MeOH)

출처 및 근거

ORD 기록
ord-fcd058c6059a403790c91f5ac095a2c6
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07112585B2

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