Picolinic acid → N,N'-bis(picolinoyl)-4,4'-diaminobenzophenone

HRID 636287노트

반응식

HRID 636287 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH:17]1[CH:18]=[CH:19][C:20]2N(O)N=[N:23][C:21]=2[CH:22]=1.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](O)=[O:34].CN([P+]([O:46]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]([NH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:22](=[O:46])[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][N:23]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)=[O:34]

참가 물질

6

반응물 4

HCID 1018Picolinic acidHCID 691494,4'-DiaminobenzophenoneHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

생성물 1

HCID 21256689N,N'-bis(picolinoyl)-4,4'-diaminobenzophenone수율 24%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4,4′-diaminobenzophenone (637 mg, 3.00 mmol) in DMF (30 mL) was added sequentially IPr2NEt (5.30 mL, 30.4 mmol), HOBt (1.23 g, 9.10 mmol), picolinic acid (1.14 g, 9.00 mmol) and BOP reagent (3.98 g, 9.0 mmol). After 17 h at room temperature, the reaction mixture was concentrated in vacuo to ca. 20 mL and added to a rapidly-stirred mixture of EtOAc (100 mL), H2O (100 mL), and sat'd NaCl (100 mL). After stirring for ca 1 h, the phases were separated and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with H2O (100 mL), dried over MgSO4, filtered, and concentrated in vacuo to a brown solid. Purification by flash chromatography (silica gel, 1% MeOH/CHCl3) afforded 303 mg (24%) of the desired product as a yellow solid. MS (ES+) m/z [M+H]+.

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo to ca. 20 mL
  2. additionadded to a rapidly-stirred mixture of EtOAc (100 mL), H2O (100 mL), and sat'd NaCl (100 mL)
  3. customthe phases were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  5. washThe combined organic layers were washed with H2O (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a brown solid
  9. customPurification by flash chromatography (silica gel, 1% MeOH/CHCl3)

출처 및 근거

ORD 기록
ord-17fa5d174ae349ab833e76bba5bbede3
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06191146B1

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