Sodium Carbonate → 3-(2-ethoxyethyl)-N-[1-(2-ethoxyethyl)-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine ethanedioate

HRID 2166135노트

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HRID 2166135 반응식
Cl[CH2:2][CH2:3][O:4][CH2:5][CH3:6].[CH2:7]([O:9][CH2:10][CH2:11][N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[N:14]=[C:13]1[NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH3:8].[C:28](=[O:31])([O-:30])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[C:5]([OH:4])(=[O:9])[C:28]([OH:30])=[O:31].[CH2:7]([O:9][CH2:10][CH2:11][N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[N:14]=[C:13]1[NH:21][CH:22]1[CH2:23][CH2:24][N:25]([CH2:2][CH2:3][O:4][CH2:5][CH3:6])[CH2:26][CH2:27]1)[CH3:8]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 31374DimethylacetamideHCID 157188163-(2-ethoxyethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine

생성물 1

HCID 1317164753-(2-ethoxyethyl)-N-[1-(2-ethoxyethyl)-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine ethanedioate수율 12.9%

시약·촉매·용매 1

HCID 962Water용매

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온도
70 °C

실험 절차

A mixture of 1.08 parts of 1-chloro-2-ethoxyethane, 2.9 parts of 3-(2-ethoxyethyl)-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine, 1.06 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at 70° C. The reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in methanol. The salt was filtered off and dried, yielding 0.7 parts (12.9%) of 3-(2-ethoxyethyl)-N-[1-(2-ethoxyethyl)-4-piperidinyl]-3H-imidazo[4,5-b]pyridin-2-amine ethanedioate(1:2); mp. 176.1° C. (compound 44).

후처리

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. filtrationThe residue was purified by filtration over silica gel using
  6. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. filtrationThe salt was filtered off
  10. customdried

출처 및 근거

ORD 기록
ord-ca4a2b26daee4154b151275ace681bd8
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04943580

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