Potassium Carbonate → Cyclopropyl-(5''-ethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

HRID 1798513노트

반응식

HRID 1798513 반응식
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:8]=[C:7]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[C:24][Si](C)(C)C)[CH:22]=3)[CH:6]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O>[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:8]=[C:7]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[CH:24])[CH:22]=3)[CH:6]=2)[CH2:2][CH2:3]1

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 68947114Cyclopropyl-(5''-trimethylsilanylethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

생성물 1

HCID 86633651Cyclopropyl-(5''-ethynyl-[2,2';4',3'']terpyridin-6'-yl)-amine

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

Cyclopropyl-(5″-trimethylsilanylethynyl-[2,2′;4′,3″]terpyridin-6′-yl)-amine (Example 2.128, step1) (1 eq, 0.127 mmol, 49 mg) is dissolved in MeOH (2 ml) and potassium carbonate is added (2 eq, 0.255 mmol, 35 mg). The reaction mixture is dissolved in EtOAc and washed with water. The organic layer is washed with brine, dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo. The crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 313.

후처리

  1. washwashed with water
  2. washThe organic layer is washed with brine
  3. customdried
  4. dry with materialover drying agent MgSO4
  5. filtrationfiltered
  6. customThe crude residue is purified by reverse phase column chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting residue is dissolved in MeOH
  9. washeluting with MeOH
  10. concentrationconcentrated in vacuo
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-7cb0218a28bb47e693f9f4cb5729e5ee
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343966B2

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