Triethylamine → HCID 178468462, 화합물

HRID 511851노트

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HRID 511851 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[CH2:11]([O:13][C:14]([C@@H:16]1[CH2:18][C@H:17]1[C:19](O)=O)=[O:15])[CH3:12].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:5]([C:4]1[CH:7]=[CH:8][C:9]2[NH:10][C:19]([CH:17]3[CH2:18][CH:16]3[C:14]([O:13][CH2:11][CH3:12])=[O:15])=[N:1][C:2]=2[CH:3]=1)#[N:6]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 7372853,4-DiaminobenzonitrileHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11535603(1R,2R)-2-(ethoxycarbonyl)cyclopropane-1-carboxylic acid

생성물 1

HCID 178468462HCID 178468462, 화합물수율 40.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 3,4-diaminobenzonitrile (326 mg, 2.45 mmol), trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid (323 mg, 2.04 mmol), and triethylamine (1.44 mL, 10.2 mmol) in DMF (10 mL) was added HBTU (1.01 g, 2.66 mmol). After stirring at room temperature for 3 h, the mixture was poured into water, and the aqueous phase was extracted with EtOAc twice. The combined organic layer was dried over sodium sulfate and concentrated in vacuo. To the residue was added acetic acid (10 mL), and the mixture was stirred at 90° C. for 12 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was poured into saturated sodium bicarbonate aqueous solution, and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to give 210 mg (40%) of the title compound as a white amorphous:

후처리

  1. extractionthe aqueous phase was extracted with EtOAc twice
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionTo the residue was added acetic acid (10 mL)
  5. stirringthe mixture was stirred at 90° C. for 12 h
  6. temperatureAfter cooling to room temperature
  7. customthe solvent was removed in vacuo
  8. additionThe residue was poured into saturated sodium bicarbonate aqueous solution
  9. extractionthe aqueous layer was extracted with EtOAc twice
  10. dry with materialThe combined organic layers were dried over sodium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-c76034939a4347c4a47e8fd3d983e274
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09101616B2

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