Ethanimidic acid, ethyl ester, hydrochloride (1:1) → N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2-methyl-1H-imidazo[4,5-b]pyridin-5-amine

HRID 2309538노트

반응식

HRID 2309538 반응식
Cl.[C:2](=[NH:7])(OCC)[CH3:3].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][C:35]3[N:40]=[C:39]([NH2:41])[C:38](N)=[CH:37][CH:36]=3)[CH2:28][CH2:27]2)=[CH:11][CH:10]=1>C(O)(=O)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[NH:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][C:35]3[N:40]=[C:39]4[N:41]=[C:2]([CH3:3])[NH:7][C:38]4=[CH:37][CH:36]=3)[CH2:28][CH2:27]2)=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 14989867N6-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-amino]-1-piperidinyl]ethyl]-2,3,6-pyridinetriamine

생성물 1

HCID 13983131N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2-methyl-1H-imidazo[4,5-b]pyridin-5-amine수율 48.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 5 parts of ethyl ethanimidate hydrochloride, 9 parts of N6 -[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2,3,6-pyridinetriamine and 100 parts of acetic acid was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was dissolved in trichloromethane. Water was added and sodium hydrogen carbonate was added till foaming had ceased. The layers were separated. The organic layer was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 4.8 parts (48.5%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-2-methyl-1H-imidazo[4,5-b]pyridin-5-amine; mp. 202.0° C. (compound 146).

후처리

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in trichloromethane
  3. additionWater was added
  4. additionsodium hydrogen carbonate was added
  5. customThe layers were separated
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from 2-propanone
  14. filtrationThe product was filtered off
  15. customdried

출처 및 근거

ORD 기록
ord-4a1f6ab354904e86a22858e460f0444d
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695569

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