5-Chloro-2-ethyl-9-methyl-13-(2-phenylethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one → 2-ethyl-9-methyl-13-(2-phenylethyl)-5-(1H-pyrrol-2-yl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

HRID 724945

반응식

HRID 724945 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.C([O-])(=O)C.[K+].C(OC([N:41]1[CH:45]=[CH:44][CH:43]=[CH:42]1)=O)(C)(C)C>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([N:10]1[C:9]2[N:15]=[CH:16][C:17]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:18][C:8]=2[C:7](=[O:27])[N:6]([CH3:28])[C:5]2[CH:4]=[CH:3][C:2]([C:42]3[NH:41][CH:45]=[CH:44][CH:43]=3)=[N:12][C:11]1=2)[CH3:14]

참가 물질

7

반응물 3

HCID 4706675-Chloro-2-ethyl-9-methyl-13-(2-phenylethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-oneHCID 517044Potassium Acetate2회HCID 643494tert-butyl 1H-pyrrole-1-carboxylate2회

생성물 1

HCID 4707432-ethyl-9-methyl-13-(2-phenylethyl)-5-(1H-pyrrol-2-yl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one수율 18.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매2회HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
125 °C

실험 절차

A mixture containing 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-(2-phenylethyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.10 g, 0.26 mmol), potassium acetate (0.05 g, 0.51 mmol), N-(tert-butyloxycarbonyl)pyrrole (0.078 g, 0.47 mmol), and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol) in 2 mL of N,N-dimethylformamide was heated in a sealed tube at 125° C. for 10 hours. Additional potassium acetate (50 mg), N-(tert-butyloxycarbonyl)pyrrole (0.08 g), and tetrakis(triphenylphosphine)palladium(0) (15 mg) were added, and the reaction mixture was heated at 140° C. for an additional 8 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated. Purification by flash chromatography, eluting with ethyl acetate/hexanes, provided 20 mg of the title compound, as a foam.

후처리

  1. temperaturethe reaction mixture was heated at 140° C. for an additional 8 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customPurification by flash chromatography
  7. washeluting with ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-b2a53aa7ba3043d680c5ca2f203e13b6
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705499

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