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Hydrochloric Acid → HCID 135867273, 화합물

HRID 2076826
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HRID 2076826 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]([NH2:15])=[NH:14])[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+].C([O:21][C:22]([C:24]1[CH:29]=[CH:28][N:27]=[N:26][C:25]=1Cl)=O)C.C([O-])([O-])=O.[K+].[K+].Cl>CO.CN(C=O)C.O>[Cl:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]2[NH:15][C:22](=[O:21])[C:24]3[CH:29]=[CH:28][N:27]=[N:26][C:25]=3[N:14]=2)[CH:6]=[CH:7][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 10942334Sodium MethoxideHCID 14542887Ethyl 3-chloropyridazine-4-carboxylateHCID 67098848HCID 67098848, 화합물

생성물 1

HCID 135867273HCID 135867273, 화합물수율 3.6%

시약·촉매·용매 3

HCID 887Methanol용매
HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

2-[2-(3-Chloro-phenyl)-ethoxy]-acetamidine hydrochloride (240 mg, 0.964 mmol; described in example 6.2) was dissolved in MeOH (2 ml) and NaOMe (30% solution in MeOH, 179 μl, 0.964 mmol) was added dropwise at 0° C. The suspension was stirred at ambient temperature for 15 min and then evaporated. To the remaining residue were added a solution of crude 3-chloro-pyridazine-4-carboxylic acid ethyl ester (180 mg) in DMF (3 ml) and subsequently K2CO3 (267 mg, 1.929 mmol) and the mixture was heated to 100° C. for 18 h. Then water was added, the pH was adjusted to 3 by addition of 0.1 N HCl and the mixture was extracted three times with CH2Cl2 and one time with ethyl acetate. The combined organic extracts were washed three times with diluted HCl (pH 3), dried (Na2SO4) and evaporated. The remaining residue was triturated with Et2O and the brown solid was filtered off and further purified by column chromatography (silica gel, CH2Cl2/MeOH 95:5) to give the title compound (11 mg, 0.035 mmol; 3.6%) as brown solid. MS: m/e=317.1 [M+H+].

후처리

  1. customevaporated
  2. temperaturethe mixture was heated to 100° C. for 18 h
  3. extractionthe mixture was extracted three times with CH2Cl2 and one time with ethyl acetate
  4. washThe combined organic extracts were washed three times with diluted HCl (pH 3)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe remaining residue was triturated with Et2O
  8. filtrationthe brown solid was filtered off
  9. customfurther purified by column chromatography (silica gel, CH2Cl2/MeOH 95:5)

출처 및 근거

ORD 기록
ord-2e2077d645d74e34899ec02bced00409
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07928106B2

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