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Citric Acid → (4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

HRID 1753039
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HRID 1753039 반응식
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15]([C:22]([C:24]2[CH:29]=[C:28]([N:30]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:27]=[CH:26][N:25]=2)=[O:23])=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[NH2:30][C:28]1[CH:27]=[CH:26][N:25]=[C:24]([C:22]([C:15]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[N:13]([C:10]([CH3:12])([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH:14]=2)=[O:23])[CH:29]=1
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참가 물질

5

반응물 3

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 90093197[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]{4-[(diphenylmethylene)amino]pyridin-2-yl}methanone

생성물 1

HCID 90093653(4-aminopyridin-2-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone수율 70.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of [1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]{4-[(diphenylmethylene)amino]pyridin-2-yl}methanone (Preparation 35, 1.4 g, 2.38 mmol) in THF (3 mL) was added a 1M solution of citric acid (2.5 g, 11.9 mmol) and the reaction was stirred at room temperature for 4 hours. A 10% aqueous solution of potassium carbonate was added carefully, and the mixture extracted into EtOAc (3×50 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. To the residue was added DCM and a solid precipitated that was filtered and dried. The mother liquors were purified using silica gel column chromatography eluting with 100% heptanes to 100% EtOAc to 5% MeOH in EtOAc to afford further material. The solids were combined to afford the title compound (70%, 710 mg).

후처리

  1. extractionthe mixture extracted into EtOAc (3×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. additionTo the residue was added DCM
  5. customa solid precipitated that
  6. filtrationwas filtered
  7. customdried
  8. customThe mother liquors were purified
  9. washeluting with 100% heptanes to 100% EtOAc to 5% MeOH in EtOAc
  10. customto afford further material

출처 및 근거

ORD 기록
ord-f70afb55b33843668ea2fa7d904a9314
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09163021B2

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